Acetyl chloride → 4-Acetyl-7-bromo-2,3,4,5-tetrahydro-3-(phenylmethyl)-1H-1,4-benzodiazepine
Reaction equation
Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH2:13]C3N=CNC=3)[CH2:11][CH2:10][N:9]([C:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)C=CC=3)=O)[CH2:8][C:7]=2[CH:31]=1.[OH-].[Na+].C(Cl)(=[O:36])C>ClCCl>[C:10]([N:9]1[CH2:8][C:7]2[CH:31]=[C:3]([Br:2])[CH:4]=[CH:5][C:6]=2[NH:12][CH2:13][CH:19]1[CH2:21][C:30]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:36])[CH3:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of Compound B (200 mg, 0.63 mmol), dichloromethane (5 mL), and aqueous sodium hydroxide (1 ml, 1N) was combined and cooled to 0° C. Acetyl chloride (66 mL, 0.94 mmol) was added to the mixture, and after stirring for 2 hour at 0° C. aqueous sodium hydroxide (20 ml, 1N) and dichloromethane (50 mL) were added, followed by extraction with dichloromethane (50 mL). The organic portions were combined, dried (Na2SO4), and concentrated to a crude oil (230 mg, 100%).
Workup
- additionwere added
- extractionfollowed by extraction with dichloromethane (50 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated to a crude oil (230 mg, 100%)
Sources & evidence
- ORD record
- ord-03212e6f4f9d4f2a982092799ff1dbf5
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06011029
Reaction notes
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