1,3-Dimethyl-2-imidazolidinone → HCID 178511217, compound

HRID 1165296Notes

Reaction equation

HRID 1165296 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8][CH2:9][CH2:10][C:11]#[N:12])[N:6]=1.Cl.[C:14](C1C=CNN=1)(=[NH:16])[NH2:15].CN1CCN(C)C1=O>O>[NH:1]([C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8][CH2:9][CH2:10][C:11]#[N:12])[N:6]=1)[C:14]([NH2:16])=[NH:15]

Participants

5

Reactant 3

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 12918379Famotidine Impurity 33HCID 178479321HCID 178479321, compound

Product 1

HCID 178511217HCID 178511217, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5 g of 3-(2-aminothiazol-4-ylmethylthio)propionitrile were added 11 g of amidinopyrazole hydrochloride and 15 ml of 1,3-dimethyl-2- imidazolidinone and the mixture was heated to 110°-120° C. for 4 hours. After cooling, 120 ml of water was added to the reaction mixture and then the product was extracted twice with 50 ml of ethyl acetate and washed. The aqueous layer thus formed was collected, added with 11 g of anhydrous potassium carbonate and 10 ml of isopropanol, the crystals thus formed were collected by filtration to provide 2.33 g of 3-(2-guanidinothiazol-4-ylmethylthio)propionitrile having a melting point of 127°-128° C.

Workup

  1. temperaturethe mixture was heated to 110°-120° C. for 4 hours
  2. temperatureAfter cooling
  3. extractionthe product was extracted twice with 50 ml of ethyl acetate
  4. washwashed
  5. customThe aqueous layer thus formed
  6. customwas collected
  7. additionadded with 11 g of anhydrous potassium carbonate and 10 ml of isopropanol
  8. customthe crystals thus formed
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-308e15272a5e4653ab66ba1aa8c86b14
Source dataset
uspto-grants-1990_03
Patent number
US04908454

Reaction notes

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