Chlorophenyl isocyanate → HCID 9951572, compound

HRID 2301507Notes

Reaction equation

HRID 2301507 reaction equation
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[C:5]([Cl:8])=[CH:6][CH:7]=1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23]>CN(C)C=O.C(OCC)(=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:22]([NH:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[Cl:14])=[O:23])=[C:3]([OH:13])[C:4]=1[S:9]([NH2:12])(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 76833Chlorophenyl isocyanateHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 9951572HCID 9951572, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (40mg, 0.18mmol) and 2-chlorophenylisocyanate (33 mg, 0.22 mmol) in 1 mL of N,N-dimethyl-formamide was stirred at room temperature for 18 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), followed by recrystallization from acetone and hexane, gave the desired product (30 mg, 44%). EI-MS (m/z) 374.3, 376.1 (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
  5. customv/v), followed by recrystallization from acetone and hexane

Sources & evidence

ORD record
ord-e5d3f8462b004940827b790ea13735cf
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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