Sodium Hydroxide → Famotidine sulfamoyl propanamide

HRID 2413346

Reaction equation

HRID 2413346 reaction equation
Cl.Cl.[NH:3]([C:7]1[S:8][CH:9]=[C:10]([CH2:12][S:13][C:14](=N)N)[N:11]=1)[C:4]([NH2:6])=[NH:5].[OH-:17].[Na+].[S:19]([NH:23][C:24](=N)[CH:25]=C)(=[O:22])(=[O:21])[NH2:20]>CO>[S:19]([NH:23][C:24](=[O:17])[CH2:25][CH2:14][S:13][CH2:12][C:10]1[N:11]=[C:7]([NH:3][C:4]([NH2:6])=[NH:5])[S:8][CH:9]=1)(=[O:22])(=[O:21])[NH2:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 178458073HCID 178458073, compoundHCID 178478807(2-Carbamimidamido-1,3-thiazol-4-yl)methyl carbamimidothioate dihydrochloride

Product 1

HCID 178512701Famotidine sulfamoyl propanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of S-(2-guanidino-4-thiazolylmethyl)isothiourea dihydrochloride (307 mg, 1.0 mmol) in methanol (5 ml) under a nitrogen atomosphere there was added 1.0 N sodium hydroxide (3 ml, 3.0 mmol). After stirring for 1/2 hour, a solution of N-sulfamyl acrylamidine (169 mg, 1.0 mol) in methanol (3 ml) was added. There was an instantaneous reaction to give product as indicated by TLC. After stirring for several hours, solvents were evaporated and the residue chromatographed on silica gel eluting with 10-15% methanol/chloroform to obtain pure product. When these fractions were combined and evaporated and the residue dissolved in a minimum amount of methanol and diluted with chloroform, the product slowly crystallized, 120 mg, mp 160°. A mixed melting point with authentic product was not depressed.

Workup

  1. customan instantaneous reaction
  2. customto give product
  3. stirringAfter stirring for several hours
  4. customsolvents were evaporated
  5. customthe residue chromatographed on silica gel eluting with 10-15% methanol/chloroform
  6. customto obtain pure product
  7. customevaporated
  8. dissolutionthe residue dissolved in a minimum amount of methanol
  9. additiondiluted with chloroform
  10. customthe product slowly crystallized

Sources & evidence

ORD record
ord-90f39c37a1bb445a8744ae80ad3f1521
Source dataset
uspto-grants-1985_01
Patent number
US04496737

Linked notes

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