Thiourea → S-[3-(dimethylamino)-2-methylpropyl]isothiourea dihydrochloride

HRID 266866Notes

Reaction equation

HRID 266866 reaction equation
[ClH:1].[Cl:2][CH2:3][CH:4]([CH3:9])[CH2:5][N:6]([CH3:8])[CH3:7].[NH2:10][C:11]([NH2:13])=[S:12]>C(O)C>[ClH:2].[ClH:1].[CH3:7][N:6]([CH3:8])[CH2:5][CH:4]([CH3:9])[CH2:3][S:12][C:11](=[NH:10])[NH2:13]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 30838413-Chloro-2-methylpropyl(dimethyl)ammonium chloride

Product 1

HCID 14219635S-[3-(dimethylamino)-2-methylpropyl]isothiourea dihydrochlorideYield 31.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-chloro-3-(dimethylamino)-2-methylpropane hydrochloride (200 g), thiourea (97.3 g) and ethanol (950 ml) was stirred and heated under reflux for 72 hours. The solution was allowed to cool and the solvent was removed in vacuo. The residue was dissolved in a small volume of ethanol and ether was added until the first permanent opalescence was observed. The mixture was stored at 4° C. for 16 hours. The solvent was removed in yacuo to afford a waxy/oily solid which was dried in vacuo over calcium chloride for 48 hours, then triturated with propan-2-ol. The resulting solid was collected by filtration, washed with propan-2-ol, and dried in vacuo to give S-[3-(dimethylamino)-2-methylpropyl]isothiourea dihydrochloride as a pale brown solid (90 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 72 hours
  3. temperatureto cool
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in a small volume of ethanol and ether
  6. additionwas added until the first permanent opalescence
  7. customThe solvent was removed in yacuo
  8. customto afford a waxy/oily solid which
  9. dry with materialwas dried in vacuo over calcium chloride for 48 hours
  10. customtriturated with propan-2-ol
  11. filtrationThe resulting solid was collected by filtration
  12. washwashed with propan-2-ol
  13. customdried in vacuo

Sources & evidence

ORD record
ord-356f33ca1c04472faeb1ef41ddca906d
Source dataset
uspto-grants-1997_07
Patent number
US05652271

Reaction notes

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