4-Chlorobenzenesulfonyl chloride → 2-{[(4-Chlorophenyl)sulfonyl]amino}-4,5-dimethoxybenzoic acid

HRID 969926ノート

反応式

HRID 969926 の反応式
C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][C:8]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>O>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:7][C:8]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])(=[O:30])=[O:29])=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 797364,5-Dimethoxyanthranilic acid

生成物 1

HCID 12399912-{[(4-Chlorophenyl)sulfonyl]amino}-4,5-dimethoxybenzoic acid収率 55%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °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. additionwere added in portions to this solution over the course of 15 min
  2. temperatureAfter the mixture had been cooled
  3. filtrationthe residue was filtered off with suction
  4. filtrationafter filtration
  5. customthe product was precipitated
  6. additionby adding 1 N hydrochloric acid

出典と根拠

ORDレコード
ord-03daae7f31ca472f9e981007dec2b78c
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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