N-bromobutanimide → 4-(Bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

HRID 1525656노트

반응식

HRID 1525656 반응식
[CH3:1][N:2]([CH3:18])[S:3]([NH:6][C:7](=[O:17])[C:8]1[CH:13]=[C:12]([F:14])[C:11]([CH3:15])=[CH:10][C:9]=1[F:16])(=[O:5])=[O:4].[Br:19]N1C(=O)CCC1=O>ClCCCl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:19][CH2:15][C:11]1[C:12]([F:14])=[CH:13][C:8]([C:7]([NH:6][S:3]([N:2]([CH3:1])[CH3:18])(=[O:5])=[O:4])=[O:17])=[C:9]([F:16])[CH:10]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimide3회HCID 89619137HCID 89619137, 화합물

생성물 1

HCID 896195864-(Bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매2회HCID 111,2-Dichloroethane용매

실험 절차

A mixture of N-[(dimethylamino)sulfonyl]-2,5-difluoro-4-methylbenzamide (Preparation 2, 0.50 g, 1.80 mmol), N-bromosuccinimide (freshly recrystallised and dried, 0.42 g, 2.34 mmol) and azobisisobutyronitrile (14.8 mg, 0.09 mmol) in 1,2-dichloroethane (15 mL) was heated under reflux with stirring whilst being irradiated with light from a 100 watt lamp. After 6 hours more N-bromosuccinimide (300 mg, 1.69 mmol) and azobisisobutyronitrile (10 mg, 0.06 mmol) were added and the mixture heated for a further 4 hours. An additional amount of N-bromosuccinimide (100 mg, 0.56 mmol) was then added and the mixture heated under reflux for a further 4 hours. The reaction mixture was cooled to room temperature and evaporated in vacuo to leave a pale yellow oil (0.54 g). Purification by silica gel column chromatography eluting with ethyl acetate/heptane 0:100-1:4 afforded the title compound (0.176 g, 27%) as a colourless oil which solidified on standing.

후처리

  1. customfreshly recrystallised
  2. customdried
  3. temperatureunder reflux
  4. customwhilst being irradiated with light from a 100 watt lamp
  5. temperaturethe mixture heated for a further 4 hours
  6. temperaturethe mixture heated
  7. temperatureunder reflux for a further 4 hours
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-1ddd56819010476e86f10678abc041c8
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085517B2

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