Acetyl chloride → HCID 178474817, compound

HRID 1902233Notes

Reaction equation

HRID 1902233 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][C:14]([NH2:16])=[NH:15])[N:9]=1)[C:2]([NH2:4])=[NH:3].C(N([CH2:22][CH3:23])CC)C.[C:24](Cl)(=[O:26])[CH3:25].C(=O)([O-])[O-:29].[K+].[K+]>CN(C)C=O.C(Cl)(Cl)Cl.O>[C:24]([NH:15][C:14](=[N:16][C:22](=[O:29])[CH3:23])[CH2:13][CH2:12][S:11][CH2:10][C:8]1[N:9]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[S:6][CH:7]=1)(=[O:26])[CH3:25]

Participants

8

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 178512221HCID 178512221, compound

Product 1

HCID 178474817HCID 178474817, compoundYield 22.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

In 10 ml of dimethylformamide was dissolved 1.2 g of 3-[2-guanidinothiazol-4-ylmethylthio]propionamidine and after adding 0.4 g of triethylamine to the solution and cooling the mixture below 15° C., a solution of 1.4 g of acetyl chloride in 3 ml of chloroform was added dropwise to the mixture. Thereafter, the mixture was stirred for 30 minutes at room temperature and then the solvent was distilled off. To the residue formed was added a solution of 0.8 g of potassium carbonate in 2 ml of water. After distilling off water, the residue was subjected to a silica gel column chromatography and the product was developed by a mixture of chloroform and methanol. Then, the eluant was distilled off to provide 0.3 g of N,N'-diacetyl-3-(2-guanidinothiazol-4-ylmethylthio)propionamidine. The product was added to a solution of 0.2 g of maleic acid in 10 ml of acetone followed by stirring for 30 minutes at room temperature. The precipitates formed were collected by filtration to provide 0.2 g of N,N'-diacetyl-3-(2-guanidinothiazol-4-ylmethylthio)-propionamidine.1/2maleate.H2O showing a melting point of 180°-181° C.

Workup

  1. temperaturecooling the mixture below 15° C.
  2. distillationthe solvent was distilled off
  3. customTo the residue formed
  4. distillationAfter distilling off water
  5. additionthe product was developed by a mixture of chloroform and methanol
  6. distillationThen, the eluant was distilled off

Sources & evidence

ORD record
ord-00107f827ac241f895e11c71901f3b78
Source dataset
uspto-grants-1982_12
Patent number
US04362736

Reaction notes

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