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

HRID 1973183Notes

Reaction equation

HRID 1973183 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, tert-butylcarbamate 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 15.4 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-65de4daf46fe466b932d27eefec1abc3
Source dataset
uspto-grants-1976_12
Patent number
US03996275

Reaction notes

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