Water → tert-butyl 7-chloro-9-(1-chloroethyl)-6-cyano-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 626841노트

반응식

HRID 626841 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 86697533tert-butyl 7-chloro-6-cyano-9-(1-hydroxyethyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

생성물 1

HCID 86697534tert-butyl 7-chloro-9-(1-chloroethyl)-6-cyano-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-16fdfb488d4544858f238e4c9e734c23
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309251B2

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