Ammonia → HCID 9966432, compound

HRID 900432Notes

Reaction equation

HRID 900432 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[C:5]([CH3:10])[C:6]=1[C:7]([NH2:9])=[O:8].ClC(Cl)(Cl)[C:20]([N:22]=C=O)=[O:21].N>C(#N)C.CO>[NH2:22][C:20]([NH:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[C:5]([CH3:10])[C:6]=1[C:7]([NH2:9])=[O:8])=[O:21]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 76400Trichloroacetyl isocyanateHCID 17930971HCID 17930971, compound

Product 1

HCID 9966432HCID 9966432, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

2-Amino-4-methyl-5-(4-chlorophenyl)-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 2M solution of ammonia in methanol (10 mL) 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. The crude product was chromatographed on silica gel eluting with dichloromethane/methanol mixtures. Trituration with ether gave the title urea (0. 1 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
  9. customThe crude product was chromatographed on silica gel eluting with dichloromethane/methanol mixtures

Sources & evidence

ORD record
ord-13f097fafba946d9a7eb54130ae623c8
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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