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

HRID 2421308Notes

Reaction equation

HRID 2421308 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-thiophenecarboxamide (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 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. waitcontinued 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-3671e59bf1c34f11a1b3efbacb0105d8
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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