Diethyl Ether → O-[3-(2,2-Dimethoxyethylthio)phenyl] N-Methylcarbamate

HRID 972116Notes

Reaction equation

HRID 972116 reaction equation
[CH3:1][O:2][CH:3]([O:13][CH3:14])[CH2:4][S:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1.[CH3:15][N:16]=[C:17]=[O:18].CCOCC>C1C=CC=CC=1.CN(C)C>[CH3:15][NH:16][C:17](=[O:18])[O:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([S:5][CH2:4][CH:3]([O:2][CH3:1])[O:13][CH3:14])[CH:7]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 12228Methyl Isocyanate2×HCID 203966733-(2,2-Dimethoxyethylthio)phenol

Product 1

HCID 20396660O-[3-(2,2-Dimethoxyethylthio)phenyl] N-Methylcarbamate

Reagents, catalysts & solvents 2

HCID 1146TrimethylamineCatalystHCID 241BenzeneSolvent2×

Procedure

3-(2,2-Dimethoxyethylthio)phenol (1.80 grams) dissolved in benzene (5 ml) was charged into a glass reaction vessel equipped with a mechanical stirrer. Methyl isocyanate (12 ml) and trimethylamine (2 drops) were then added, and the resulting mixture was stirred at room temperature for a period of about 51/2 hours. The mixture was then allowed to stand overnight and was then stripped of excess methyl isocyanate and a portion of the benzene. The concentrated solution was then added to ether and cooled to -60° C., resulting in a precipitate. The precipitate was recrystallized from ether to yield the desired product O-[3-(2,2-dimethoxyethylthio)phenyl]-0 N-methylcarbamate having a melt point of 46° to 48° C.

Workup

  1. additionwas charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. waitto stand overnight
  4. temperaturecooled to -60° C.
  5. customresulting in a precipitate
  6. customThe precipitate was recrystallized from ether

Sources & evidence

ORD record
ord-506e16f2806c491f9af80d5252fa702a
Source dataset
uspto-grants-1979_07
Patent number
US04163112

Reaction notes

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