Phenyl thioxochloroformate → 2-Isothiocyanato-4-methoxy-6-methylpyrimidine

HRID 330446Notes

Reaction equation

HRID 330446 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH:10][Si](C)(C)C)[N:4]=1.C1C=CC(O[C:22](Cl)=[S:23])=CC=1>C1(C)C=CC=CC=1>[N:10]([C:5]1[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([CH3:9])[N:6]=1)=[C:22]=[S:23]

Participants

4

Reactant 2

HCID 70498Phenyl thioxochloroformateHCID 135876394-Methoxy-6-methyl2-trimethylsilylaminopyrimidine

Product 1

HCID 142756782-Isothiocyanato-4-methoxy-6-methylpyrimidineYield 63.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4.2 g of 4-methoxy-6-methyl-2-trimethylsilylaminopyrimidine and 3.5 g of phenyl chlorothionocarbonate in 30 ml of toluene is stirred with heating at ca. 80° C. for 5.5 hours. The reaction solution is cooled to room temperature and filtered to remove the precipitate. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel chromatography (eluent: ethyl acetate: toluene =1:3) to give the title compound (2.3 g). mp 54°~55° C.

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. filtrationfiltered
  3. customto remove the precipitate
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe residue is purified by silica gel chromatography (eluent: ethyl acetate: toluene =1:3)

Sources & evidence

ORD record
ord-09ed0ef466724d298214983b1f0b370d
Source dataset
uspto-grants-1990_01
Patent number
US04897105

Reaction notes

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