Ammonia → HCID 19383040, compound

HRID 1768520Notes

Reaction equation

HRID 1768520 reaction equation
[C:1]([NH:9][C:10]1[CH:14]=[CH:13][S:12][C:11]=1[C:15]([O:17]C)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:19]>CO.C1COCC1>[C:1]([NH:9][C:10]1[CH:14]=[CH:13][S:12][C:11]=1[C:15]([NH2:19])=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 222Ammonia2×HCID 738341methyl 3-(benzoylamino)-2-thiophenecarboxylate

Product 1

HCID 19383040HCID 19383040, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 14.21 g (54.4 mmol) of crude methyl 3-(benzoylamino)-2-thiophenecarboxylate in 100 mL of methanol and 100 mL of THF was added 100 mL of concentrated aqueous ammonia. The mixture was stirred at room temperature for 5 days and an additional 100 mL of concentrated aqueous ammonia was added. After stirring for 5 more days the mixture was rotovapped to remove the bulk of the organic solvents and the residue was extracted with two 125 mL portions of ethyl acetate. The insoluble material was collected by filtration and combined with the residue from evaporating the ethyl acetate extracts to dryness to furnish 11.96 g (89%) of crude 3-(benzoylamino)-2-thiophenecarboxamide as a tan solid. 1H-NMR (d6-DMSO) δ 7.55(3H,m), 7.7(1H,d), 7.95(2H,m), 8.18(1H,d).

Workup

  1. stirringAfter stirring for 5 more days the mixture
  2. customto remove the bulk of the organic solvents
  3. extractionthe residue was extracted with two 125 mL portions of ethyl acetate
  4. filtrationThe insoluble material was collected by filtration
  5. customfrom evaporating the ethyl acetate

Sources & evidence

ORD record
ord-b1c74e45e6c74bafa407804a4f5bba80
Source dataset
uspto-grants-1995_01
Patent number
US05378678

Reaction notes

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