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

HRID 448907ノート

反応式

HRID 448907 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-5e4d1df35e2440a5ac48a5f0c223e81e
出典データセット
uspto-grants-2013_07
特許番号
US08481738B2

反応ノート

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