Sodium Hydroxide → 3-(2-Thiazolyl)propylguanidine hemisulphate

HRID 917957Notes

Reaction equation

HRID 917957 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH2:7][CH2:8][NH2:9].[OH-].[Na+].[S:12]([O-:16])([O-:15])(=[O:14])=[O:13].CS[C:19]([NH2:21])=[NH2+:20].CS[C:24]([NH2:26])=[NH2+:25]>C(OCC)(=O)C>[S:12]([OH:16])([OH:15])(=[O:14])=[O:13].[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH2:7][CH2:8][NH:9][C:19]([NH2:21])=[NH:20].[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH2:7][CH2:8][NH:9][C:24]([NH2:26])=[NH:25]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6604939S-methyl isothiourea hemisulfateHCID 116869213-(1,3-Thiazol-2-yl)propan-1-amine

Product 1

HCID 1785127923-(2-Thiazolyl)propylguanidine hemisulphate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-(2-Thiazolyl)propylamine (2.7 g) (prepared from the amine dihydrochloride by reaction with aqueous sodium hydroxide and extraction with ethyl acetate) is mixed intimately with finely powdered S-methylthiouronium sulphate (5.3 g) and the mixture is heated at 140°-150°C for 1 hour. After cooling, the mass is extracted with hot ethanol several times, and the combined extracts are diluted with ether which causes the precipitation of a white solid. Recrystallization from aqueous ethanol yields 3-(2-thiazolyl)propylguanidine hemisulphate, m.p. 160°-163°C.

Workup

  1. temperaturethe mixture is heated at 140°-150°C for 1 hour
  2. temperatureAfter cooling
  3. extractionthe mass is extracted with hot ethanol several times
  4. additionthe combined extracts are diluted with ether which
  5. customthe precipitation of a white solid
  6. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-bc568d28cc0c418687bbec3dd218b2e6
Source dataset
uspto-grants-1976_07
Patent number
US03968216

Reaction notes

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