Propargyl bromide → Methyl Isocyanate

HRID 483629Notes

Reaction equation

HRID 483629 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]([CH2:7][C:8]#[CH:9])[C:3]1=[O:10].C(OC(OCC)CN)C.C(Br)C#C>>[CH2:7]([N:4]1[CH:5]=[CH:6][NH:2][C:3]1=[O:10])[C:8]#[CH:9].[CH3:1][N:2]=[C:3]=[O:10]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 695242,2-DiethoxyethylamineHCID 150655051,3-Dihydro-1-methyl-3-(2-propyn-1-yl)-2H-imidazol-2-one

Product 2

HCID 12228Methyl IsocyanateHCID 19753286HCID 19753286, compound

Procedure

The 1,3-dihydro-1-(2-propynyl)-2H-imidazol-2-one intermediates were prepared as outlined in Scheme 2 for the synthesis of 1,3-dihydro-1-methyl-3-(2-propynyl)-2H-imidazol-2-one (X). Aminoacetaldehyde diethyl acetal was reacted with propargylbromide to give a mixture of the tertiary and secondary amines VII and VIII which were separated by chromatography on silica gel. Treatment of VIII with methyl isocyanate gave IX and this was heated in aqueous oxalic acid to give 1-methyl-3-(2-propynyl)-2H-imidazol-2-one (X).

Workup

  1. customto give
  2. customwere separated by chromatography on silica gel

Sources & evidence

ORD record
ord-2ad07dbf005e4cd8850397bd6136b89c
Source dataset
uspto-grants-1993_07
Patent number
US05225567

Reaction notes

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