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

HRID 1934973ノート

反応式

HRID 1934973 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒2 回HCID 6344Dichloromethane溶媒

実験手順

A stirred mixture of 4-[(3-bromophenyl)-N-acetylamino]-8-methyl-6-nitro-3-quinolinecarbonitrile (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) δ 5.19 (dd, CH2Br).

後処理

  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

出典と根拠

ORDレコード
ord-5252d63abc6c41a190def99fc74c7167
出典データセット
uspto-grants-2002_05
特許番号
US06384051B1

反応ノート

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