Ammonia → HCID 9858651, compound

HRID 900440Notes

Reaction equation

HRID 900440 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:5]([C:10]([F:13])([F:12])[F:11])[C:6]=1[C:7]([NH2:9])=[O:8].ClC(Cl)(Cl)[C:22]([N:24]=C=O)=[O:23].N>O1CCCC1.CO>[NH2:24][C:22]([NH:1][C:2]1[S:3][C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:5]([C:10]([F:11])([F:13])[F:12])[C:6]=1[C:7]([NH2:9])=[O:8])=[O:23]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 76400Trichloroacetyl isocyanateHCID 17930983HCID 17930983, compound

Product 1

HCID 9858651HCID 9858651, compoundYield 36.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-4-trifluoromethyl-5-phenyl-3-thiophenecarboxamide (0.35 g) was suspended in tetrahydrofuran (10 ml) and trichloroacetylisocyanate (0.19 g) was added dropwise with stirring over 5 minutes. Stirring was continued for 1 h at room temperature and then a 2M solution of ammonia in methanol (10 ml) was added and stirring continued for a further 12 h. A precipitate formed and was filtered off and washed with ethyl acetate (5 ml) to give the title urea (0.12 g).

Workup

  1. stirringStirring
  2. waitwas continued for 1 h at room temperature
  3. stirringstirring
  4. waitcontinued for a further 12 h
  5. customA precipitate formed
  6. filtrationwas filtered off
  7. washwashed with ethyl acetate (5 ml)

Sources & evidence

ORD record
ord-08d9f04e99404e7483fc1e8745354393
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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