Carbon Tetrachloride → 8-Bromomethyl-4-[(3-bromophenyl)-N-acetylamino]-6-nitro-3-quinolinecarbonitrile

HRID 379115노트

반응식

HRID 379115 반응식
[Br:1][C:2]1[CH:3]=[C:4]([N:8]([C:12]2[C:21]3[C:16](=[C:17]([CH3:25])[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=3)[N:15]=[CH:14][C:13]=2[C:26]#[N:27])[C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[Br:28]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl.S(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:28][CH2:25][C:17]1[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[C:21]2[C:16]=1[N:15]=[CH:14][C:13]([C:26]#[N:27])=[C:12]2[N:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:9](=[O:11])[CH3:10]

참가 물질

7

반응물 4

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 224667474-[(3-Bromophenyl)-N-acetylamino]-8-methyl-6-nitro-3-quinolinecarbonitrileHCID 23665763Sodium Bisulfite

생성물 1

HCID 224666528-Bromomethyl-4-[(3-bromophenyl)-N-acetylamino]-6-nitro-3-quinolinecarbonitrile수율 119%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매2회HCID 6344Dichloromethane용매

실험 절차

A stirred mixture of 4-[(3-bromophenyl)-N-acetylamino]-8-methyl-6-nitro-quinoline-3-carbonitrile (10.6 g, 25 mmol), N-bromosuccinimide (6.68 g, 37.5 mmol), 0.30 g of dibenzoyl peroxide, and 200 ml of carbon tetrachloride was refluxed for 2 h, treated with an additional 0.30 g of dibenzoyl peroxide, and refluxed an additional 2.5 h, cooled, diluted with methylene chloride, and stirred with aqueous sodium bisulfite. The organic layer was separated and washed successively with water, sodium bicarbonate solution, and water. The solution was dried and evaporated to give 15 g of a white foam, NMR (CDCl3) d 5.19 (dd, CH2Br).

후처리

  1. temperaturewas refluxed for 2 h
  2. temperaturerefluxed an additional 2.5 h
  3. temperaturecooled
  4. customThe organic layer was separated
  5. washwashed successively with water, sodium bicarbonate solution, and water
  6. customThe solution was dried
  7. customevaporated

출처 및 근거

ORD 기록
ord-b4a50898b65e4d50961de3be23819a7e
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297258B1

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