Dimethylamine → S-2-[4-(1-methylpropoxy)phenoxy]ethyl N,N-dimethylthiocarbamate

HRID 2248194Notes

Reaction equation

HRID 2248194 reaction equation
[CH3:1][NH:2][CH3:3].C(N(CC)CC)C.[C:11](=[S:13])=[O:12].[CH3:14][CH:15]([O:18][C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25]Br)=[CH:21][CH:20]=1)[CH2:16][CH3:17]>C(O)(C)(C)C>[CH3:1][N:2]([CH3:3])[C:11](=[O:12])[S:13][CH2:25][CH2:24][O:23][C:22]1[CH:27]=[CH:28][C:19]([O:18][CH:15]([CH3:14])[CH2:16][CH3:17])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 10039Carbonyl SulfideHCID 156625902-[4-(1-Methylpropoxy)phenoxy]ethyl bromide

Product 1

HCID 14552670S-2-[4-(1-methylpropoxy)phenoxy]ethyl N,N-dimethylthiocarbamate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Following procedure C in H. Tilles, JACS 81:714 (1959) a solution of dimethylamine (0.58 ml, 8.79 mmol) and triethylamine (1.22 ml, 8.79 mmol) in 3ml of t-butyl alcohol is cooled to 15°, after which carbonylsulfide (0.71 g, 11.87 mmol) is passed in which vigorous stirring. The solution is then warmed to 30°, with stirring, 2-[4-(1-methylpropoxy)phenoxy]ethyl bromide (2.40 g, 8.79 mmol) is added rapidly. The reaction mixture is heated slowly to 50° and maintained at 50° for 3 hours. The solvent is then distilled off and the product is worked up to give S-2-[4-(1-methylpropoxy)phenoxy]ethyl N,N-dimethylthiocarbamate (compound 36, Table B).

Workup

  1. temperatureThe solution is then warmed to 30°
  2. temperatureThe reaction mixture is heated slowly to 50°
  3. temperaturemaintained at 50° for 3 hours
  4. distillationThe solvent is then distilled off

Sources & evidence

ORD record
ord-39bc637285114b1d9e5a939404e5d245
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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