Methyl Isocyanate → alpha-[1-Methyl-imidazolin-2-yl]-alpha-(O-methylaminocarbonyloximino)-acetonitrile

HRID 67995Notes

Reaction equation

HRID 67995 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][N:4]=[C:3]1[C:7](=[N:10][OH:11])[C:8]#[N:9].[CH3:12][N:13]=[C:14]=[O:15]>C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][N:2]1[CH2:6][CH2:5][N:4]=[C:3]1[C:7](=[N:10][O:11][C:14]([NH:13][CH3:12])=[O:15])[C:8]#[N:9]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 136408868HCID 136408868, compound

Product 1

HCID 54502986alpha-[1-Methyl-imidazolin-2-yl]-alpha-(O-methylaminocarbonyloximino)-acetonitrile

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

15.2 g (0.1 mol) of α-[1-methyl-imidazolin-2-yl]-α-oximino-acetonitrile and 6.4 g (0.11 mol) of methyl isocyanate are stirred in 200 ml of ethyl acetate with a few drops of triethylamine for 16 hours. 16 g (76.5% of theory) of end product are filtered off and this is washed with a little ethyl acetate; melting point 186°-190° C. (decomposition).

Workup

  1. filtration16 g (76.5% of theory) of end product are filtered off
  2. washthis is washed with a little ethyl acetate

Sources & evidence

ORD record
ord-563082784fd84d21889ae659a32ea804
Source dataset
uspto-grants-1982_08
Patent number
US04347372

Reaction notes

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