Chlorosulfonyl isocyanate → 5-Phenyl-2-Ureidothiophene-3-Carboxamide

HRID 900424Notes

Reaction equation

HRID 900424 reaction equation
ClS([N:5]=[C:6]=[O:7])(=O)=O.[NH2:8][C:9]1[S:10][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][C:13]=1[C:14]([NH2:16])=[O:15]>C1(C)C=CC=CC=1>[NH2:5][C:6]([NH:8][C:9]1[S:10][C:11]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:12][C:13]=1[C:14]([NH2:16])=[O:15])=[O:7]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 7039652-Amino-5-phenylthiophene-3-carboxamide

Product 1

HCID 64197655-Phenyl-2-Ureidothiophene-3-Carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Chlorosulphonylisocyanate (0.081 mL) was added to a stirred suspension at 0° C. of 2-amino-5-phenyl-3-thiophenecarboxamide (0.2 g) in toluene (10 mL). After stirring for 16 h at room temperature, the solvent was evaporated and the residue dissolved in acetonitrile (20 mL). 10% Sodium bicarbonate solution (2 mL) was added and the mixture was stirred for 1 h. After acidification with 2M hydrochloric acid, the solution was extracted three times with ethyl acetate. The combined extracts were dried (MgSO4) and the solvent was evaporated. Chromatography on silica eluting with methanol/dichloromethane mixtures gave the title urea (0.027 g).

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe residue dissolved in acetonitrile (20 mL)
  3. addition10% Sodium bicarbonate solution (2 mL) was added
  4. stirringthe mixture was stirred for 1 h
  5. extractionAfter acidification with 2M hydrochloric acid, the solution was extracted three times with ethyl acetate
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b2a0d844086a4018bd039a5ed7ead35c
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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