3-Chlorophenyl isothiocyanate → HCID 178446857, compound

HRID 1287416Notes

Reaction equation

HRID 1287416 reaction equation
C[O-].[Na+].Cl.[C:5]([NH2:11])(=[NH:10])[CH2:6][CH2:7][CH2:8][CH3:9].[Cl:12][C:13]1[CH:14]=[C:15]([N:19]=[C:20]=[S:21])[CH:16]=[CH:17][CH:18]=1>C(O)C>[Cl:12][C:13]1[CH:14]=[C:15]([NH:19][C:20]([NH:10][C:5](=[NH:11])[CH2:6][CH2:7][CH2:8][CH3:9])=[S:21])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 754493-Chlorophenyl isothiocyanateHCID 10942334Sodium MethoxideHCID 11615174Pentanimidamide Hydrochloride

Product 1

HCID 178446857HCID 178446857, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred, ice bath chilled solution of 5.4 g. of sodium methoxide in 100 ml. of absolute ethyl alcohol was added slowly 13.69 g. of valeramidine hydrochloride. Stirring was continued for ten minutes and then 16.9 g. of 3-chlorophenyl isothiocyanate was added dropwise and stirring was continued an additional hour. The solvent was evaporated under reduced pressure, the resulting residue was taken up in 100 ml. of dry ether and the ether solution was extracted several times with water and the combined water wash was extracted with 50 ml. dry ether. The combined ether extract was dried and then acidified by addition of 50 ml. 2-N ethereal hydrogen chloride. The resulting precipitate was filtered to give, after recrystallization from acetonitrile, 9.6 g. of 1-(3-chlorophenyl)-3-(pentanimidoyl)-2-thiourea hydrochloride; m.p. 142°-145°C.

Workup

  1. temperatureTo a stirred, ice bath chilled solution of 5.4 g
  2. waitwas continued for ten minutes
  3. stirringstirring
  4. waitwas continued an additional hour
  5. customThe solvent was evaporated under reduced pressure
  6. extractionof dry ether and the ether solution was extracted several times with water
  7. washthe combined water wash
  8. extractionwas extracted with 50 ml
  9. extractionThe combined ether extract
  10. customwas dried
  11. additionacidified by addition of 50 ml
  12. filtrationThe resulting precipitate was filtered
  13. customto give
  14. customafter recrystallization from acetonitrile, 9.6 g

Sources & evidence

ORD record
ord-595077c2bed74c70b23667f1e780146d
Source dataset
uspto-grants-1976_10
Patent number
US03984467

Reaction notes

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