Acetonitrile → HCID 11708357, compound
Reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9](#N)[CH3:10]>>[CH2:5]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH2:8])[CH2:6][CH2:1][CH2:2][CH2:3][CH2:4][CH2:9][CH3:10]Participants
Procedure
Into 500 ml of acetonitrile was suspended 50.9 g (0.1 mol) of the phenylenediamine derivative obtained in the foregoing process (2) in an atmosphere of nitrogen. The suspension was cooled with ice to 5° C. or lower where it was then kept. To the suspension was then added 55.8 ml (0.4 mol) of triethylamine. To the reaction mixture was then added dropwise 11.5 g (0.1 mol) of thiophosgene while the temperature of the reaction system was being controlled to lower than 10° C. After completion of the dropwise addition, the temperature of the reaction solution was gradually returned to room temperature. The reaction solution was then allowed to undergo at the same temperature for 2 hours. To the reaction solution was then added a mixture of ethyl acetate and water. The reaction solution was then subjected to separation. The organic phase thus extracted was dried, and then concentrated to obtain 29.4 g of a crude reaction product in the form of oil. The crude reaction product was then purified through a column filled with a 1/5 mixture of ethyl acetate and hexane to obtain 12.6 g (0.048 mol) of the desired benzimidazole (yield: 48%).
Sources & evidence
- ORD record
- ord-f4c595471cc443a4a3538d8795f55f39
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06074813
Reaction notes
Loading…