Ethanol → Dimaprit hydrochloride

HRID 266865Notes

Reaction equation

HRID 266865 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 hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-chloro-3-(dimethylamino)propane hydrochloride (200 g), thiourea (98.1 g) and ethanol (11) was stirred and heated under reflux for 25 hours. The solution was cooled to ambient temperature and ethyl acetate added until permanent opalescence was obtained. The mixture was stored at 4° C. overnight then filtered to give S-[3-(dimethylamino)propyl]isothiourea dihydrochloride as a colourless solid. (283 g), m.p. 155°-159° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 25 hours
  3. customwas obtained
  4. filtrationthen filtered

Sources & evidence

ORD record
ord-46b82e97efc7465abd875062f6e51b31
Source dataset
uspto-grants-1997_07
Patent number
US05652271

Reaction notes

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