2-Bromophenyl isocyanate → HCID 9868309, compound

HRID 2301502Notes

Reaction equation

HRID 2301502 reaction equation
[CH3:1][N:2]([CH3:15])[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].[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]=[C:24]=[O:25]>CN(C)C=O.C(OCC)(=O)C>[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C:24]([NH:13][C:8]1[CH:9]=[CH:10][C:11]([Cl:12])=[C:6]([S:3]([N:2]([CH3:15])[CH3:1])(=[O:5])=[O:4])[C:7]=1[OH:14])=[O:25]

Participants

5

Reactant 2

HCID 1370972-Bromophenyl isocyanateHCID 23447758N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

Product 1

HCID 9868309HCID 9868309, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N,N-dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide (80 mg, 0.32 mmol) and 2-bromophenylisocyanate (47 μL, 0.38 mmol) in 2 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 (20/80, v/v), followed by recrystallization from ethyl acetate and hexane, gave the desired product (88 mg, 62%). EI-MS (m/z) 446.2, 448.3, 450.3 (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 (20/80
  5. customv/v), followed by recrystallization from ethyl acetate and hexane

Sources & evidence

ORD record
ord-bfd9ec68b8704f62be060275029aa72a
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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