Phosphorus pentachloride → 2-(4-Chloro-phenylsulfonylamino)4,5-dimethoxy-benzoyl chloride

HRID 969927ノート

反応式

HRID 969927 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:13]=2[C:14](O)=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:26]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:13]=2[C:14]([Cl:26])=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 24819Phosphorus pentachlorideHCID 12399912-{[(4-Chlorophenyl)sulfonyl]amino}-4,5-dimethoxybenzoic acid

生成物 1

HCID 98433672-(4-Chloro-phenylsulfonylamino)4,5-dimethoxy-benzoyl chloride収率 93%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
42.5 °C

実験手順

33.71 g (0.32 mol) of sodium carbonate were dissolved in 250 ml of water and heated to 60° C. 25.00 g (0.13 mol) of 2-amino-4,5-dimethoxybenzoic acid were introduced into the solution, and 29.55 g (0.14 mol) of 4-chlorobenzenesulfonyl chloride were added in portions to this solution over the course of 15 min. After the mixture had been cooled, the residue was filtered off with suction and taken up in 1% strength sodium bicarbonate solution and, after filtration, the product was precipitated by adding 1 N hydrochloric acid. 25.90 g (55%) of 2-(4-chlorophenylsulfonylamino)-4,5-dimethoxybenzoic acid of melting point 212-214° C. were obtained. 25.90 g (0.07 mol) of 2-(4-chlorophenylsulfonylamino)-4,5-dimethoxybenzoic acid were suspended in 75 ml of toluene and, after addition of 17.30 g (0.08 mol) of phosphorus pentachloride, the mixture was stirred at 40-45° C. for 2.5 h. It was then concentrated to half the volume in vacuo, and the precipitated product was filtered off with suction and washed with a little toluene. 25.30 g (93%) of 2-(4-chlorophenylsulfonylamino)-4,5-dimethoxybenzoyl chloride, of melting point 175-177° C., were obtained.

後処理

  1. concentrationIt was then concentrated to half the volume in vacuo
  2. filtrationthe precipitated product was filtered off with suction
  3. washwashed with a little toluene

出典と根拠

ORDレコード
ord-a032261eebc245fe8cf431747f462475
出典データセット
uspto-grants-2007_12
特許番号
US07309579B2

反応ノート

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