Water → 4-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide

HRID 1844639

반응식

HRID 1844639 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[Cl:11].Cl.CN(C)CCCN=C=NCC.[CH3:24][Si:25]([CH2:28][NH2:29])([CH3:27])[CH3:26].O>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:29][CH2:28][Si:25]([CH3:27])([CH3:26])[CH3:24])=[O:7])=[CH:4][C:3]=1[Cl:11]

참가 물질

6

반응물 4

HCID 962WaterHCID 874881-(Trimethylsilyl)methylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 125943024-Bromo-3-chlorobenzoic acid

생성물 1

HCID 668366994-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 4-bromo-3-chloro-benzoic acid (commercially available) (5.0 g) in dichloromethane (30 ml) was added N-(−3-dimethylaminopropyl)-N′-ethylcarbodiimid hydrochloride (5.29 g), N,N-dimethylaminopyridine (1.19 g) and trimethylsilylmethylamine (2.85 ml). The reaction mixture was stirred at ambient temperature for 5 hours. Water and dichloromethane was added to the reaction mixture. The phases were separated and the organic phase was washed with brine, dried over sodium sulfate and filtered through silica gel. The reaction mixture was concentrated to give 4-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide (4.87 g). 1H-NMR (400 MHz, CDCl3): 7.68 (d, 1H), 7.55 (s, 1H), 7.33 (d, 1H), 5.85 (s, 1H), 2.84 (d, 2H), 0.00 (s, 9H) ppm.

후처리

  1. customThe phases were separated
  2. washthe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered through silica gel
  5. concentrationThe reaction mixture was concentrated

출처 및 근거

ORD 기록
ord-a3c1a6b6daf04fb9b085f17a021f3c52
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946447B2

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