Phosgene → [6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]isocyanate
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([CH3:15])([CH3:14])[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:6]=2[C:23]=1[Cl:24].[C:25](Cl)(Cl)=[O:26].C(N(CC)CC)C>ClCCCl>[Cl:24][C:23]1[C:6]2[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])=[N:8][C:9]([CH3:15])([CH3:14])[C:10](=[O:13])[N:11]([CH3:12])[C:5]=2[CH:4]=[CH:3][C:2]=1[N:1]=[C:25]=[O:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3.5 g (0.01 mol) of 7-amino-6-chloro-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one in 60 ml of 1,2-dichloroethane is added dropwise while stirring to a solution of 1.5 g (0.015 mol) of phosgene in ice-cooled 1,2-dichloroethane so that the reaction temperature does not exceed 10°. Subsequently, the reaction mixture is heated at reflux while stirring for a further 10 minutes, whereupon it is cooled to ca 10° and made basic with triethylamine. There is thus obtained a solution of [6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]isocyanate which can be stored in the cold for several hours with the exclusion of moisture. It is further processed without isolation of the isocyanate contained therein.
Workup
- customdoes not exceed 10°
- temperatureSubsequently, the reaction mixture is heated
- temperatureat reflux
- temperatureis cooled to ca 10°
Sources & evidence
- ORD record
- ord-5c51df54ecca46888d2a7437799e94cd
- Source dataset
- uspto-grants-1983_03
- Patent number
- US04377522
Reaction notes
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