NaNCO → 2-[(Aminocarbonyl)amino]-4-methyl-5-phenyl-3-thiophenecarboxamide

HRID 900443Notes

Reaction equation

HRID 900443 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([CH3:10])[C:6]=1[C:7]([NH2:9])=[O:8].[N-:17]=[C:18]=[O:19].[Na+]>C(O)(=O)C.O>[NH2:17][C:18]([NH:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([CH3:10])[C:6]=1[C:7]([NH2:9])=[O:8])=[O:19]

Participants

5

Reactant 2

HCID 11051568NaNCOHCID 179309582-Amino-4-methyl-5-phenyl-3-thiophencarboxamide

Product 1

HCID 98568152-[(Aminocarbonyl)amino]-4-methyl-5-phenyl-3-thiophenecarboxamideYield 14.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 2-amino-4-methyl-5-phenyl-3-thiophencarboxamide (0.18 g) in glacial acetic acid (5 mL) and water (0.5 mL) was added sodium isocyanate (101 mg). The resulting solution was stirred at room temperature for 4 h and then poured into water. The precipitate was filtered off and washed with more water. The product was chromatographed on silica gel eluting with dichloromethane/methanol mixtures to give the title product as a solid (30 mg).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with more water
  3. customThe product was chromatographed on silica gel eluting with dichloromethane/methanol

Sources & evidence

ORD record
ord-9781cb43da804ff7b73ce344a89931f9
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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