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

HRID 2301506노트

반응식

HRID 2301506 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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−).

후처리

  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

출처 및 근거

ORD 기록
ord-d7d628bc042f47309995c95d4d8e016f
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06500863B1

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