Methyl Isocyanate → 4-phenoxyphenoxyacetone oxime N-methyl carbamate

HRID 35280Notes

Reaction equation

HRID 35280 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[O:5]([C:12]1[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18](=[N:20][OH:21])[CH3:19])=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N1(C2CCCCCCC2)CCCCCCN1>C(#N)C>[CH3:1][NH:2][C:3](=[O:5])[OH:4].[O:5]([C:12]1[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18](=[N:20][OH:21])[CH3:19])=[CH:14][CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 66583054DiazabicyclooctaneHCID 867423654-Phenoxyphenoxyacetone oxime

Product 1

HCID 867423674-phenoxyphenoxyacetone oxime N-methyl carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

With stirring, a solution of 3.42 g of methyl isocyanate in 10 ml of acetonitrile is added dropwise over 30 minutes at room temperature to a solution of 12.85 g (0.05 mole) of 4-phenoxyphenoxyacetone oxime and 0.05 g of diazabicyclooctane in 90 ml of acetonitrile. After stirring for 7 hours at 40° C., the solvent is distilled off by rotary evaporation and the residue is purified by chromatography over 200 g of silica gel (eluant: a 3:1 mixture of diethyl ether and hexane). The main fraction is subsequently recrystallised in diethyl ether, affording 4-phenoxyphenoxyacetone oxime N-methyl carbamate (compound 5) of the formula ##STR20## with a melting point of 60°-62° C.

Workup

  1. stirringAfter stirring for 7 hours at 40° C.
  2. distillationthe solvent is distilled off by rotary evaporation
  3. customthe residue is purified by chromatography over 200 g of silica gel (eluant
  4. additiona 3:1 mixture of diethyl ether and hexane)
  5. customThe main fraction is subsequently recrystallised in diethyl ether

Sources & evidence

ORD record
ord-643b01dea2674eb2a7a94347b074a886
Source dataset
uspto-grants-1988_08
Patent number
US04766152

Reaction notes

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