Ethanol → Dimaprit hydrochloride

HRID 266881Notes

Reaction equation

HRID 266881 reaction equation
[ClH:1].[Cl:2][CH2:3][CH2:4][CH2:5][N:6]([CH3:8])[CH3:7].[NH2:9][C:10]([NH2:12])=[S:11].C(O)C>C(OCC)(=O)C>[ClH:2].[ClH:1].[CH3:7][N:6]([CH3:8])[CH2:5][CH2:4][CH2:3][S:11][C:10](=[NH:9])[NH2:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 2723790Thiourea

Product 1

HCID 90045Dimaprit hydrochlorideYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 1-chloro-3-(dimethylamino) propane hydrochloride (305.7 g), thiourea (150 g) and ethanol (1530 ml) was heated under reflux for 24 hours then cooled to ambient temperature. Ethyl acetate was added until a faint opalescence was observed, then the mixture was stored at 4° C. for 72 hours. The resulting solid was collected by filtration, washed with ethyl acetate, and dried in vacuo at 40° C. to give S-[3-(dimethylamino)propyl]isothiourea dihydrochloride as a white solid (403 g), m.p. 155°-157° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with ethyl acetate
  5. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-d879c6ecc91548d8a9020fa25c28e991
Source dataset
uspto-grants-1997_07
Patent number
US05652271

Reaction notes

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