1,2-Dichloro-3-isocyanatobenzene → N-[4-chloro-2-hydroxy-3-(N''-methylaminosulfonyl)phenyl]-N'-(2,3-dichlorophenyl) urea

HRID 2301506ノート

反応式

HRID 2301506 の反応式
[CH3:1][NH:2][S:3]([C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([NH2:13])[C:7]=1[OH:14])(=[O:5])=[O:4].[Cl:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[N:23]=[C:24]=[O:25]>CN(C)C=O.C(OCC)(=O)C>[Cl:12][C:11]1[CH:10]=[CH:9][C:8]([NH:13][C:24]([NH:23][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=2[Cl:15])=[O:25])=[C:7]([OH:14])[C:6]=1[S:3]([NH:2][CH3:1])(=[O:5])=[O:4]

参加物

5

反応物 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 18373530N-Methyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

生成物 1

HCID 10137198N-[4-chloro-2-hydroxy-3-(N''-methylaminosulfonyl)phenyl]-N'-(2,3-dichlorophenyl) urea収率 49%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of N-methyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide (70 mg, 0.29 mmol) and 2,3-dichlorophenylisocyanate (57 μL, 0.44 mmol) in 2 mL of N,N-dimethylformamide was stirred at room temperature for 66 hours. The mixture was diluted with ethyl acetate and washed with water to give the crude material. Purification by column chromatography on silica gel, eluting with ethyl acetate/hexane (30/70, v/v), gave the desired product (60 mg, 49%, three steps). EI-MS (m/z) 422.3, 424.3, 426.3 (M−).

後処理

  1. washwashed with water
  2. customto give the crude material
  3. customPurification by column chromatography on silica gel
  4. washeluting with ethyl acetate/hexane (30/70

出典と根拠

ORDレコード
ord-d7d628bc042f47309995c95d4d8e016f
出典データセット
uspto-grants-2002_12
特許番号
US06500863B1

反応ノート

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