Methyl Isocyanate → 2-(N-Methylcarbamoyl)thio-5-chloropyrimidine

HRID 905229Notes

Reaction equation

HRID 905229 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[S:8])[NH:6][CH:7]=1.[CH3:9][N:10]=[C:11]=[O:12]>ClCCl>[CH3:9][NH:10][C:11]([S:8][C:5]1[N:6]=[CH:7][C:2]([Cl:1])=[CH:3][N:4]=1)=[O:12]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 71403455-Chloro-2(1H)-pyrimidinethione

Product 1

HCID 204757402-(N-Methylcarbamoyl)thio-5-chloropyrimidineYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-chloropyrimidine-2-thione (3 mmol) and methylisocyanate (4 mmol) in dichloromethane (15 ml) was stirred at room temperature for 2 h, the solvent was then distilled off and the residue was crystallised from CHCl3 : Pet. ether; yield 85%, m.p. 115° C. 1H NMR (CDCl3) δ3.03 (Me), 8.62 (H-4, H-6).

Workup

  1. distillationthe solvent was then distilled off
  2. customthe residue was crystallised from CHCl3

Sources & evidence

ORD record
ord-a5bf9179c33d4bd596882dd04d0c11ed
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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