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

HRID 2301506Notes

Reaction equation

HRID 2301506 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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−).

Workup

  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

Sources & evidence

ORD record
ord-d7d628bc042f47309995c95d4d8e016f
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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