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NH2 (CH3CH2)2NH CH;CO2H, CH3COONA PHCH3, 110 C Lidocaine 2,6-dimethylaniline (2) What is the limiting reagent in step 1? What is the theoretical yield of amide 1 in figure 3? What is the theoretical yield of Lidocaine? Base calculations on 2,6-dimethylaniline?

NH2 (CH3CH2)2NH CH;CO2H, CH3COONA PHCH3, 110 C Lidocaine 2,6-dimethylaniline (2) What is the limiting reagent in step 1? What is the theoretical yield of amide 1 in figure 3? What is the theoretical yield of Lidocaine? Base calculations on 2,6-dimethylaniline?

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ISBN:9781305957404
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LAB 12: SYNTHESIS OF LIDOCAINE Experimental Procedure Step 2: Preparation of Lidocaine, 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide – Step 1- Preparation of N-(2,6-Dimethylphenyl)chloroacetamide 1. To a pre-weighed 50-ml round bottomed flask, add the pressed-dry amide 1 and re-weigh the flask to get an exact amount of amide 1. 1. measure out 3.0 mL of 2,6- dimethylaniline into a 10-mL graduated cylinder and set aside in your hood. 2. sequentially add 7.5 mL diethylamine, 25 mL toluene and a few boiling stones. Attach a water-cooled reflux condenser to the round bottomed flask. 2. measure out 15-ml of glacial acetic acid and add it to a 125 mL Erlenmeyer flask. 3. Reflux the reaction mixture for 60 min. 3. Add the amine (2,6- dimethylaniline), via a Pasteur pipet, to the acetic acid in the Erlenmeyer flask. 4. Cool to room temperature, Transfer to a separatory funnel and wash the organic layer with 3x50 mL portions of 4. Transfer 2 mL of 2-chloroacetyl chloride to the Erlenmeyer flask containing acetic acid and 2,6- dimethylaniline. water. 5. Extract the organic layer with 3M HCI (2x20 mL). Remove aqueous layer into a new Erlenmeyer and wash organic layer in separatory funnel with water (1x20 ml). Drain aqueous layer into the acidic extract just performed. Cool this flask in an ice-bath and add a thermometer to the solution. 4. Add 25 ml of 0.333 M aqueous sodium acetate to the Erlenmeyer flask. 5. Stir thoroughly for 10 minutes using your glass stir rod. 6. When it has reached 10 °C, add a small portion of 3M NaOH. Continue to add 3M NaOH, in portions, while 6. Isolate the product via vacuum filtration using a Buchner funnel on the common bench. Rinse with a few keeping the temperature below 20 °C until the solution is strongly basic (green by pH paper). portions of the remaining cold water. Press as dry as possible with another piece of filter paper. 7. Product is precipitating in the solution. la NH2 (CH;CH2)2NH CH;CO2H, CH3COONA PHCH3, 110 C Lidocaine 2,6-dimethylaniline (2) What is the limiting reagent in step 1? What is the theoretical yield of amide 1 in figure 3? What is the theoretical yield of Lidocaine? Base calculations on 2,6-dimethylaniline? How many molar equivalents of diethyl amine are used in step 2?
Transcribed Image Text:LAB 12: SYNTHESIS OF LIDOCAINE Experimental Procedure Step 2: Preparation of Lidocaine, 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide – Step 1- Preparation of N-(2,6-Dimethylphenyl)chloroacetamide 1. To a pre-weighed 50-ml round bottomed flask, add the pressed-dry amide 1 and re-weigh the flask to get an exact amount of amide 1. 1. measure out 3.0 mL of 2,6- dimethylaniline into a 10-mL graduated cylinder and set aside in your hood. 2. sequentially add 7.5 mL diethylamine, 25 mL toluene and a few boiling stones. Attach a water-cooled reflux condenser to the round bottomed flask. 2. measure out 15-ml of glacial acetic acid and add it to a 125 mL Erlenmeyer flask. 3. Reflux the reaction mixture for 60 min. 3. Add the amine (2,6- dimethylaniline), via a Pasteur pipet, to the acetic acid in the Erlenmeyer flask. 4. Cool to room temperature, Transfer to a separatory funnel and wash the organic layer with 3x50 mL portions of 4. Transfer 2 mL of 2-chloroacetyl chloride to the Erlenmeyer flask containing acetic acid and 2,6- dimethylaniline. water. 5. Extract the organic layer with 3M HCI (2x20 mL). Remove aqueous layer into a new Erlenmeyer and wash organic layer in separatory funnel with water (1x20 ml). Drain aqueous layer into the acidic extract just performed. Cool this flask in an ice-bath and add a thermometer to the solution. 4. Add 25 ml of 0.333 M aqueous sodium acetate to the Erlenmeyer flask. 5. Stir thoroughly for 10 minutes using your glass stir rod. 6. When it has reached 10 °C, add a small portion of 3M NaOH. Continue to add 3M NaOH, in portions, while 6. Isolate the product via vacuum filtration using a Buchner funnel on the common bench. Rinse with a few keeping the temperature below 20 °C until the solution is strongly basic (green by pH paper). portions of the remaining cold water. Press as dry as possible with another piece of filter paper. 7. Product is precipitating in the solution. la NH2 (CH;CH2)2NH CH;CO2H, CH3COONA PHCH3, 110 C Lidocaine 2,6-dimethylaniline (2) What is the limiting reagent in step 1? What is the theoretical yield of amide 1 in figure 3? What is the theoretical yield of Lidocaine? Base calculations on 2,6-dimethylaniline? How many molar equivalents of diethyl amine are used in step 2?
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