Ammonia → HCID 22318910, compound

HRID 497308Notes

Reaction equation

HRID 497308 reaction equation
CO[C:3](=[NH:34])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:33])[NH:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([S:29](=[O:32])(=[O:31])[NH2:30])=[CH:25][CH:24]=3)=[CH:16][CH:15]=2)=[O:12])[CH:5]=1.[NH3:35]>>[C:3]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:12])[NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([S:29](=[O:32])(=[O:31])[NH2:30])=[CH:25][CH:24]=3)=[O:33])=[CH:18][CH:19]=2)[CH:7]=[CH:8][CH:9]=1)(=[NH:34])[NH2:35]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 69732515HCID 69732515, compound

Product 1

HCID 22318910HCID 22318910, compound

Procedure

3-{3-[4-(4-Sulfamoylbenzylcarbamoyl)-phenyl]-ureido}-benzimidic acid methyl ester (370 mg) was dissolved in methanolic ammonia solution (5 ml, 7 M) and refluxed for 4 h. The mixture was filtered, the filtrate concentrated in vacuo and diethylether was added. The resulting precipitate (300 mg) was filtered off. 100 mg were suspended in ethyl acetate/methanol/ammonia, filtered off, washed with ethyl acetate and ether and dried in vacuo to yield 60 mg of 4-[3-(3-carbamimidoylphenyl)-ureido]-N-(4-sulfamoylbenzyl)-benzamide.

Workup

  1. temperaturerefluxed for 4 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo and diethylether
  4. additionwas added
  5. filtrationThe resulting precipitate (300 mg) was filtered off
  6. filtrationfiltered off
  7. washwashed with ethyl acetate and ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-305d3d7175c842e59c824451daf379de
Source dataset
uspto-grants-2005_09
Patent number
US06949567B2

Reaction notes

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