Ammonia → 2-(Carbamoylamino)thiophene-3-carboxamide

HRID 11421

Reaction equation

HRID 11421 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].ClC(Cl)(Cl)[C:12]([N:14]=C=O)=[O:13].N>C(#N)C.CO>[NH2:14][C:12]([NH:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8])=[O:13]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 76400Trichloroacetyl isocyanateHCID 6994952-Aminothiophene-3-carboxamide

Product 1

HCID 111714022-(Carbamoylamino)thiophene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

2-Amino-3-thiophencarboxamide (0.44 g) was suspended in acetonitrile (25 ml) and trichloroacetylisocyanate (0.2 ml) added dropwise with stirring over 10 minutes. Stirring was continued for a further 3 h at room temperature and then a solution of ammonia in methanol (10 ml of a 2M solution) was added and stirring was continued for a further 2 h. The solvent was evaporated and the residue treated with water. The resultant solid was filtered off and washed with more water. Trituration with ether gave the title urea (0.2 g).

Workup

  1. stirringStirring
  2. waitwas continued for a further 3 h at room temperature
  3. stirringstirring
  4. waitwas continued for a further 2 h
  5. customThe solvent was evaporated
  6. additionthe residue treated with water
  7. filtrationThe resultant solid was filtered off
  8. washwashed with more water

Sources & evidence

ORD record
ord-f0c8411110a14024be0381e63896f360
Source dataset
uspto-grants-2006_08
Patent number
US07098240B2

Linked notes

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