4-Bromobutyronitrile → 3-bromo-4-chloro-N-[2-(3-cyano-propoxy)-phenyl]-N-methyl-benzamide

HRID 661660노트

반응식

HRID 661660 반응식
Br[CH2:2][CH2:3][CH2:4][C:5]#[N:6].[Br:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:11]([N:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])[CH3:14])=[O:12]>CN(C=O)C>[Br:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:11]([N:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:2][CH2:3][CH2:4][C:5]#[N:6])[CH3:14])=[O:12]

참가 물질

4

반응물 2

HCID 214124-BromobutyronitrileHCID 686031173-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide

생성물 1

HCID 686031543-bromo-4-chloro-N-[2-(3-cyano-propoxy)-phenyl]-N-methyl-benzamide수율 92.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

CsCO3 (5.17 g, 15.87 mmol) was added to a solution of 4-bromo-butyronitrile (0.63 mL, 6.35 mmol) and 3-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide (1.80 g, 5.29 mmol, Step 3B) in DMF (20 mL). The mixture was stirred at room temperature for approximately 16 hrs and was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, washed with water and brine, and was dried over MgSO4. The organic filtrate was evaporated to yield 3-bromo-4-chloro-N-[2-(3-cyano-propoxy)-phenyl]-N-methyl-benzamide as a light yellow solid (2.0 g). MS [M+H]+: 408.9; tR=2.39 min. (method 1)

후처리

  1. customwas partitioned between ethyl acetate and water
  2. customThe ethyl acetate layer was separated
  3. washwashed with water and brine
  4. dry with materialwas dried over MgSO4
  5. customThe organic filtrate was evaporated

출처 및 근거

ORD 기록
ord-d5ee6cc5385f4cb8ae06d5eca1ddf1a0
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084614B2

반응 노트

불러오는 중…