Methyl Isocyanate → HCID 20396666, compound

HRID 972112Notes

Reaction equation

HRID 972112 reaction equation
[CH3:1][O:2][CH:3]([O:13][CH3:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH3:15][N:16]=[C:17]=[O:18]>C(N(CC)CC)C.C1C=CC=CC=1>[CH3:15][NH:16][C:17](=[O:18])[O:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]([O:2][CH3:1])[O:13][CH3:14])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 20396656HCID 20396656, compound

Product 1

HCID 20396666HCID 20396666, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 241BenzeneSolvent

Procedure

4-(2,2-Dimethoxyethoxy)phenol (5.0 grams) and benzene were charged into a glass reaction vessel equipped with a mechanical stirrer. Methyl isocyanate (3.5 ml) and 4 drops of triethylamine were then added, and the reaction mixture was stirred at room temperature for a period of about 6 hours. After this time the reaction mixture was filtered, and the filtrate was concentrated to 10 ml by partially stripping the solvent under reduced pressure. Cyclohexane (10 ml) was then added to the concentrate, resulting in the formation of a precipitate. The precipitate was recovered by filtration to yield the desired product O-[4-(2,2-dimethoxyethoxy)phenyl] N-methylcarbamate as a slightly pink solid melting at 79° to 81° C.

Workup

  1. customequipped with a mechanical stirrer
  2. filtrationAfter this time the reaction mixture was filtered
  3. concentrationthe filtrate was concentrated to 10 ml
  4. additionCyclohexane (10 ml) was then added to the concentrate
  5. customresulting in the formation of a precipitate
  6. filtrationThe precipitate was recovered by filtration

Sources & evidence

ORD record
ord-facb03be78b44c1b87e773c470681d4f
Source dataset
uspto-grants-1979_07
Patent number
US04163112

Reaction notes

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