Guanidine Hydrochloride → N-carbamimidoyl-4-chloro-3-sulfamoylbenzamide;hydrochloride

HRID 486599Notes

Reaction equation

HRID 486599 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[Cl:6][C:7]1[CH:16]=[CH:15][C:10]([C:11](OC)=[O:12])=[CH:9][C:8]=1[S:17](=[O:20])(=[O:19])[NH2:18].C[O-].[Na+].[Na]>CO>[ClH:6].[Cl:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([NH:4][C:3]([NH2:5])=[NH:2])=[O:12])=[CH:9][C:8]=1[S:17](=[O:19])(=[O:20])[NH2:18]

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 4277179Methyl 4-chloro-3-sulfamoylbenzoateHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 178479492N-carbamimidoyl-4-chloro-3-sulfamoylbenzamide;hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.5 g of guanidine hydrochloride and then 5 g of methyl 4-chloro-3-sulfamoylbenzoate are added to a methanolic sodium methoxide solution, prepared from 1.9 g of sodium in 90 ml of methanol. After heating this mixture to 50°-60° C. under inert gas (nitrogen or argon) over the course of 30 hours, the solvent is removed by distillation, the solution is adjusted to pH 6 after taking up the residue with 2N acetic acid and is extracted with ethyl acetate. After acidifying the dried extract (drying over magnesium sulfate) using ethereal hydrochloric acid, the title compound is filtered off.

Workup

  1. temperatureAfter heating this mixture to 50°-60° C. under inert gas (nitrogen or argon) over the course of 30 hours
  2. customthe solvent is removed by distillation
  3. extractionis extracted with ethyl acetate
  4. extractionextract
  5. dry with material(drying over magnesium sulfate)
  6. filtrationthe title compound is filtered off

Sources & evidence

ORD record
ord-07160572845d4c3cb6efc05bda6be417
Source dataset
uspto-grants-1994_03
Patent number
US05292755

Reaction notes

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