Dimethylformamide → 4-(4-Phenylquinazolin-2-ylamino)benzoyl chloride

HRID 406822

反応式

HRID 406822 の反応式
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]([NH:17][C:18]3[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.S(Cl)([Cl:34])=O>ClCCl>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]([NH:17][C:18]3[CH:26]=[CH:25][C:21]([C:22]([Cl:34])=[O:23])=[CH:20][CH:19]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 7764484-[(4-Phenylquinazolin-2-yl)amino]benzoic acid

生成物 1

HCID 576629364-(4-Phenylquinazolin-2-ylamino)benzoyl chloride

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of 4-(4-phenylquinazolin-2-ylamino)benzoic acid (1.19 g, 3.49 mmol), prepared as described in Example 10, in dichloromethane (50 mL) was added a catalytic amount of dimethylformamide (100 μL) and thionyl chloride (1.50 mL, 20.6 mmol), and the resulting mixture was stirred at rt overnight. The solid was filtered, washed with hexanes, and dried under reduced pressure (high vacuum) to give the product (4-(4-phenylquinazolin-2-ylamino)benzoyl chloride) as a yellow solid (1.21 g, 97%). This material was then added portionwise to a solution of commercially available 3-amino-4-methylbenzyl alcohol (600 mg, 4.37 mmol), and triethylamine (1.0 mL, 7.2 mmol) in dichloromethane (50 mL) that had been cooled to 0° C. in an ice bath. The mixture was allowed to warm to rt overnight, then the solid was collected by filtration, washed with saturated sodium bicarbonate and water and dried under reduced pressure to give N-(5-hydroxymethyl-2-methylphenyl)-4-(4-phenylquinazolin-2-ylamino)benzamide as a pure yellow solid (1.33 g, 86%).

後処理

  1. customprepared
  2. filtrationThe solid was filtered
  3. washwashed with hexanes
  4. customdried under reduced pressure (high vacuum)

出典と根拠

ORDレコード
ord-710c6e078875434d965a07b76d88a980
出典データセット
uspto-grants-2014_06
特許番号
US08754092B2

関連ノート

読み込み中…