Ammonia → HCID 67556690, compound

HRID 342463Notes

Reaction equation

[C:1]([C:4]1[CH:14]=[C:13]([NH:15][C:16](=[O:25])[C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:24])[C:7]2[O:8][C:9]([CH3:12])=[C:10]([CH3:11])[C:6]=2[CH:5]=1)(O)=[O:2].C([N:28](CC)CC)C.ClC(OCC(C)C)=O.N>ClCCl.CO>[C:1]([C:4]1[CH:14]=[C:13]([NH:15][C:16](=[O:25])[C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:24])[C:7]2[O:8][C:9]([CH3:12])=[C:10]([CH3:11])[C:6]=2[CH:5]=1)(=[O:2])[NH2:28]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of 5-carboxy-7-(2,6-dichlorobenzoylamino)-2,3-dimethylbenzo[b]furan (152 mg) and triethylamine (61 mg) in dichloromethane (3 ml) was stirred at -20° C. and to the solution was added isobutyl chloroformate (66 mg). The mixture was stirred at -20° C. for 3 hours and added to cold (-20° C.) solution of 10% ammonia in methanol (3 ml). The reaction mixture was stirred at ambient temperature for 10 minutes and partitioned between dichloromethane and water. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from ethyl acetate to give 5-carbamoyl-7-(2,6-dichlorobenzoylamino)-2,3-dimethylbenzo[b]furan (70 mg).

Workup

stirringThe reaction mixture was stirred at ambient temperature for 10 minutes
custompartitioned between dichloromethane and water
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel
customthe obtained oil was crystallized from ethyl acetate

Sources & evidence

ORD record: ord-51ca44eebeeb43d5a45500e9dadd8f0b
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05858995

Reaction notes

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