Methyl Isocyanate → HCID 20441645, compound

HRID 1632963Notes

Reaction equation

HRID 1632963 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[Cl:5][C:6]1[CH:7]=[N:8][C:9](=[O:12])[NH:10][CH:11]=1>CN(C)C=O.C(N(CC)CC)C>[CH3:1][NH:2][C:3]([N:10]1[CH:11]=[C:6]([Cl:5])[CH:7]=[N:8][C:9]1=[O:12])=[O:4]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 1085785-Chloro-2(1H)-pyrimidinone

Product 1

HCID 20441645HCID 20441645, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Methyl isocyanate (56.5 ml) was added dropwise over 15 minutes, with cooling, to a stirred solution of 5-chloropyrimidin-2-one (25 g) in N,N-dimethylformamide (290 ml) and triethylamine (30.4 ml). The temperature of the reaction mixture was kept at approximately 22° C. The mixture was stirred at room temperature for a further 40 minutes and then cooled in an ice bath. The solid was collected, washed with cold dichloromethane (4×215 ml), briefly air dried and then dried in vacuo at room temperature to give the title compound as white crystals (33.36 g), m.p. 241°-243° C. decomp. U.V. data: λmaxEtOH 230 nm (ε10,370), 322.5 mm (ε1,700).

Workup

  1. customwas kept at approximately 22° C
  2. temperaturecooled in an ice bath
  3. customThe solid was collected
  4. washwashed with cold dichloromethane (4×215 ml), briefly air
  5. customdried
  6. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-4c8a9e1887954fb9acde2e4b7410d94c
Source dataset
uspto-grants-1984_10
Patent number
US04478839

Reaction notes

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