Dimethylamine → Thiourea, N'-(3-hydroxyphenyl)-N,N-dimethyl-

HRID 1076288Notes

Reaction equation

HRID 1076288 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[S:10])[CH:5]=[CH:6][CH:7]=1.[C:11]([NH:15][C:16](=[O:18])[O-:17])([CH3:14])([CH3:13])[CH3:12].CNC>CO>[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([N:15]([CH3:16])[CH3:11])=[S:10])[CH:5]=[CH:6][CH:7]=1.[C:11]([NH:15][C:16](=[O:17])[O-:18])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 8200263-isothiocyanatophenolHCID 21252905Tert-butylcarbamate

Product 2

HCID 5368133Thiourea, N'-(3-hydroxyphenyl)-N,N-dimethyl-HCID 21252905Tert-butylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
15 °C

Procedure

1-(meta-hydroxyphenyl)-3,3-dimethyl-2-thiourea, tertbutylcarbamate is prepared by charging to a suitable vessel about 25 g. (approximately 0.1 mole) meta-hydroxyphenyl isothiocyanate, tert-butylcarbamate dissolved in about 150 ml. of methanol, and adding, with stirring about 154 g. (approximately 0.12 moles) of 40 percent aqueous dimethylamine mixed with about 50 ml. of methanol in a single increment. The mass quickly solidifies as the temperature rises from about room temperature to about 60°C. The mass is cooled to about 15°C., separated from the residual liquid by filtration, washed with four 150 ml. portions of a 75 percent methanol/25 percent water solution and dried under vacuum overnight.

Workup

  1. customby charging to a suitable vessel
  2. customrises from about room temperature to about 60°C
  3. customseparated from the residual liquid by filtration
  4. washwashed with four 150 ml
  5. dry with materialportions of a 75 percent methanol/25 percent water solution and dried under vacuum overnight

Sources & evidence

ORD record
ord-6d39d2c9fa2743f29cca32e1a8c46bdf
Source dataset
uspto-grants-1976_05
Patent number
US03956384

Reaction notes

Loading…