Ethyl Acetate → HCID 19031565, compound

HRID 266875Notes

Reaction equation

HRID 266875 reaction equation
[ClH:1].[Cl:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:10][CH2:11][CH3:12])[CH2:7][CH2:8][CH3:9].[NH2:13][C:14]([NH2:16])=[S:15].C(OCC)(=O)C>C(O)C>[ClH:2].[ClH:1].[CH2:7]([N:6]([CH2:10][CH2:11][CH3:12])[CH2:5][CH2:4][CH2:3][S:15][C:14](=[NH:13])[NH2:16])[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2723790ThioureaHCID 19031570HCID 19031570, compound

Product 1

HCID 19031565HCID 19031565, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A stirred mixture of 1-chloro-3-(dipropylamino)-propane hydrochloride (42 g), thiourea (15.5 g) and ethanol (250 ml) was heated under reflux for 24 hours then allowed to cool to ambient temperature. Ethyl acetate was added until a faint opalescence was observed, then the mixture was stored at 4° C. for 24 hours. After this time it had deposited an oil which was isolated by decantation of the bulk of the solvent followed by removal of residual solvent in vacuo. The oil was triturated with ethanol, the solvent was removed by decantation, and the residue was dried in vacuo at ambient temperature for 24 hours to give a pale brown solid. The ethanol solution decanted from the oil was concentrated in vacuo, and the residue was triturated with ethanol as described above to give a second crop of pale brown solid. The ethanol solution remaining after isolation of the second crop was concentrated in vacuo and the residue was triturated with propan-2-ol to give a third crop of solid. The three crops were combined to give S-[3-(dipropylamino)propyl]isothiourea dihydrochloride as a pale brown solid (51 g), m.p 143°-145° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customwas isolated by decantation of the bulk of the solvent
  4. customfollowed by removal of residual solvent in vacuo
  5. customThe oil was triturated with ethanol
  6. customthe solvent was removed by decantation
  7. customthe residue was dried in vacuo at ambient temperature for 24 hours
  8. customto give a pale brown solid
  9. customThe ethanol solution decanted from the oil
  10. concentrationwas concentrated in vacuo
  11. customthe residue was triturated with ethanol
  12. customto give a second crop of pale brown solid
  13. concentrationwas concentrated in vacuo
  14. customthe residue was triturated with propan-2-ol
  15. customto give a third crop of solid

Sources & evidence

ORD record
ord-f6d3de83853a46daba4470827eb4a7fc
Source dataset
uspto-grants-1997_07
Patent number
US05652271

Reaction notes

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