3-Amino-5-(4-fluorophenyl)thiophene-2-carboxamide → 3-[(Aminocarbonyl)amino]-5-(4-fluorophenyl)-2-thiophenecarboxamide

HRID 900418Notes

Reaction equation

HRID 900418 reaction equation
[N-:1]=[C:2]=[O:3].[Na+].[NH2:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[S:8][C:7]=1[C:18]([NH2:20])=[O:19]>C(O)(=O)C.O>[NH2:1][C:2]([NH:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[S:8][C:7]=1[C:18]([NH2:20])=[O:19])=[O:3]

Participants

5

Reactant 2

HCID 27829033-Amino-5-(4-fluorophenyl)thiophene-2-carboxamideHCID 11051568NaNCO

Product 1

HCID 98171243-[(Aminocarbonyl)amino]-5-(4-fluorophenyl)-2-thiophenecarboxamideYield 13.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Sodium isocyanate (1.08 g) was added portionwise to a stirred suspension of 3-amino-5-(4-fluorophenyl)-2-thiophenecarboxamide (3.2 g) in acetic acid (150 mL) and water (90 mL). After 20 h, the solid was filtered off and washed with water, methanol and ether. Recrystallisation from methanol/dimethylsulphoxide gave the title urea (0.5 g) as a 1:1 dimethylsulphoxide solvate.

Workup

  1. filtrationthe solid was filtered off
  2. washwashed with water, methanol and ether
  3. customRecrystallisation from methanol/dimethylsulphoxide

Sources & evidence

ORD record
ord-980b78b90efd4c4692f839fc19df05d9
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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