Thiourea → S-(4-dimethylaminomethyl-2-pyridylmethyl)isothiourea trihydrochloride

HRID 1382767Notes

Reaction equation

HRID 1382767 reaction equation
[ClH:1].Cl.[Cl:3][CH2:4][C:5]1[CH:10]=[C:9]([CH2:11][N:12]([CH3:14])[CH3:13])[CH:8]=[CH:7][N:6]=1.[NH2:15][C:16]([NH2:18])=[S:17]>C(O)C>[ClH:3].[ClH:1].[ClH:3].[CH3:13][N:12]([CH2:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:4][S:17][C:16](=[NH:15])[NH2:18])[CH:10]=1)[CH3:14]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 132926032-Chloromethyl-4-dimethylaminomethylpyridine dihydrochloride

Product 1

HCID 21273288S-(4-dimethylaminomethyl-2-pyridylmethyl)isothiourea trihydrochlorideYield 125%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloromethyl-4-(dimethylaminomethyl)pyridine dihydrochloride (14.67 g) was added to a refluxing solution of thiourea (4.34 g) in ethanol (120 ml) and the solution refluxed for 3 hours, whereupon solid precipitated. After cooling the mixture (ice bath), the solid was filtered and recrystallised from methanolethanol to give S-(4-dimethylaminomethyl-2-pyridylmethyl)isothiourea trihydrochloride (11.88 g), m.p. 175°-9° C.

Workup

  1. temperaturethe solution refluxed for 3 hours, whereupon solid
  2. customprecipitated
  3. temperatureAfter cooling the mixture (ice bath)
  4. filtrationthe solid was filtered
  5. customrecrystallised from methanolethanol

Sources & evidence

ORD record
ord-4bda33e3c7da4ac080b2556f1600d523
Source dataset
uspto-grants-1989_02
Patent number
US04808589

Reaction notes

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