Benzenesulfonic Acid → 4-Carbamoylimidazolium 5-olate

HRID 1183796Notes

Reaction equation

HRID 1183796 reaction equation
[C:1]1([S:7]([OH:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][CH:12]([C:16]([NH2:18])=[O:17])[C:13]([NH2:15])=[O:14].O.[C:20]1(S(O)(=O)=O)C=CC=CC=1.C(OC)(OC)OC>C(O)C>[C:1]1([S:7]([OH:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:20]1[NH:11][C:12]([C:13]([NH2:15])=[O:14])=[C:16]([OH:17])[N:18]=1

Participants

7

Reactant 4

HCID 7371Benzenesulfonic AcidHCID 9005Trimethyl orthoformateHCID 964572-AminopropanediamideHCID 15619088Hydroxybenzenesulfonic acid

Product 2

HCID 7371Benzenesulfonic AcidHCID 1243434-Carbamoylimidazolium 5-olateYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a suspension of benzenesulfonic acid salt of 2-aminomalonamide [4] (1.20 g; 4.37 mmol) prepared above and benzenesulfonic acid monohydrate (81 mg; 0.46 mmol) in dry ethanol (100 ml) was added trimethyl orthoformate (1.9 ml; 17.4 mmol), and was refluxed for 2 hours under an argon atmosphere. The resulting white suspension was stirred overnight at room temperature and the precipitates were collected by filtration to give colorless benzenesulfonic acid salt of SM-108 (1.02 g; 3.58 mmol; yield 82%), which was identical with that obtained in Example 2.

Workup

  1. temperaturewas refluxed for 2 hours under an argon atmosphere
  2. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-89a35ac613174ff7ba10406a8b3ea7f5
Source dataset
uspto-grants-2014_03
Patent number
US08664405B2

Reaction notes

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