Water → tert-butyl 7-chloro-9-(1-chloroethyl)-6-cyano-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22](O)[CH3:23])[C:5]2[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][C:6]=2[C:19]=1[C:20]#[N:21].CN(C)C=O.S(Cl)([Cl:32])=O.O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]([Cl:32])[CH3:23])[C:5]2[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][C:6]=2[C:19]=1[C:20]#[N:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The tert-butyl 7-chloro-6-cyano-9-(1-hydroxyethyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (0.090 g, 0.26 mmol) was dissolved in methylene chloride (3 mL) and N,N-dimethylformamide (0.020 mL) and cooled in an ice bath. The thionyl chloride (0.037 mL, 0.51 mmol) was added slowly, and the reaction was stirred for 1 h and then diluted with methylene chloride (30 mL). The reaction mixture was cooled in an ice bath, and water saturated sodium bicarbonate was added. The organic layer was washed with water, brine, dried over magnesium sulfate, and concentrated to give tert-butyl 7-chloro-9-(1-chloroethyl)-6-cyano-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate as an oil. LCMS calculated for C17H20Cl2N2O3Na (M+Na)+: m/z=393.1; found: 393.0.
Workup
- temperatureThe reaction mixture was cooled in an ice bath
- washThe organic layer was washed with water, brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-16fdfb488d4544858f238e4c9e734c23
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309251B2
Reaction notes
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