2-(Dimethylamino)ethanol → N,N1-Dimethyl-S-(2-dimethylaminoethyl)isothiourea

HRID 1395642Notes

Reaction equation

HRID 1395642 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4]O.[CH3:7][N:8]([CH3:12])[C:9]([NH2:11])=[S:10]>Br>[CH3:7][N:8]([CH3:12])[C:9](=[NH:11])[S:10][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1]

Participants

4

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 30341921,1-Dimethyl-2-thiourea

Product 1

HCID 86736996N,N1-Dimethyl-S-(2-dimethylaminoethyl)isothioureaYield 128%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 2-dimethylaminoethanol (2.23 g), N,N1 -dimethylthiourea (2.6 g) and aqueous hydrobromic acid (48%, 20 ml) was boiled under reflux for 50 hours and evaporated to dryness. The residue was recrystallised from a mixture of methanol and ethanol to give the dihydrobromide of the title compound (5.6 g) m.p. 198°-199°. (Found: C, 24.9; H, 5.7; N, 12.7; S, 9.5; Br, 47.2; C7H17N3S.2HBr requires: C, 24.9; H, 5.7; N, 12.5; S, 9.5; Br, 47.4%)

Workup

  1. temperatureunder reflux for 50 hours
  2. customevaporated to dryness
  3. customThe residue was recrystallised from a mixture of methanol and ethanol

Sources & evidence

ORD record
ord-a9a1fe4f0811404da64771351a41c312
Source dataset
uspto-grants-1980_05
Patent number
US04205071

Reaction notes

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