Methyl Isocyanate → (E)-Methomyl

HRID 2286144Notes

Reaction equation

HRID 2286144 reaction equation
C[N:2]1[CH2:6]CC[C:3]1=[O:7].[CH3:8]/[C:9](/[S:12][CH3:13])=[N:10]/[OH:11].CN=C=O>C(N(CC)CC)C>[CH3:8]/[C:9](/[S:12][CH3:13])=[N:10]\[O:11][C:3]([NH:2][CH3:6])=[O:7]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 13387N-methyl-2-pyrrolidoneHCID 639157519125-12-3

Product 1

HCID 5353758(E)-MethomylYield 96%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 256 g portion of an N-methyl pyrrolidone solution of methomyl oxime (containing 0.4 mole MMO) and 0.5 g triethylamine was charged to a 500 ml 5-necked flask. To this was added 28.7 g (0.5 mole) methyl isocyanate rapidly. The temperature rose to 40° C. for 1.0 hour. The reaction mixture was then transferred to a Kugelrohr apparatus, and the solvent removed at reduced pressure. A yield of 96% Methomyl, assaying >99% was realized.

Workup

  1. customthe solvent removed at reduced pressure

Sources & evidence

ORD record
ord-541423b6e8454b9592a13eb69fc2c450
Source dataset
uspto-grants-1982_04
Patent number
US04327033

Reaction notes

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