1,2-Dichloro-3-isocyanatobenzene → N-[3-(N''-allylaminosulfonyl)4-chloro-2-hydroxyphenyl]-N'-(2,3-dichlorophenyl) urea

HRID 2301522Notes

Reaction equation

HRID 2301522 reaction equation
[CH2:1]([NH:4][S:5]([C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([NH2:15])[C:9]=1[OH:16])(=[O:7])=[O:6])[CH:2]=[CH2:3].[Cl:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[N:25]=[C:26]=[O:27]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([NH:4][S:5]([C:8]1[C:9]([OH:16])=[C:10]([NH:15][C:26]([NH:25][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([Cl:24])[C:18]=2[Cl:17])=[O:27])[CH:11]=[CH:12][C:13]=1[Cl:14])(=[O:7])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 18373522n-Allyl-3-amino-6-chloro2-hydroxybenzenesulfonamide

Product 1

HCID 11554208N-[3-(N''-allylaminosulfonyl)4-chloro-2-hydroxyphenyl]-N'-(2,3-dichlorophenyl) ureaYield 29.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of crude N-allyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide (20 mg) and 2,3-dichlorophenylisocyanate (12 μL, 0.09 mmol) in 1 mL of N,N-dimethylformamide was stirred at room temperature for 20 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 (10 mg, 29% for two steps). EI-MS (m/z) 450.2, 452.2, 454.1 (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-862394e73e3f4c2ea3e7db68ee184385
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

Loading…