Phenyl thioxochloroformate → 2-Isothiocyanato-4,6-dimethoxypyrimidine

HRID 330447

Reaction equation

HRID 330447 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][Si](C)(C)C)[N:4]=1.C1C=CC(O[C:23](Cl)=[S:24])=CC=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([N:11]=[C:23]=[S:24])[N:4]=1

Participants

4

Reactant 2

HCID 70498Phenyl thioxochloroformateHCID 198683124,6-Dimethoxy-N-(trimethylsilyl)pyrimidin-2-amine

Product 1

HCID 142539422-Isothiocyanato-4,6-dimethoxypyrimidineYield 43.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 45.0 g of 4,6-dimethoxy-2-trimethylsilylaminopyrimidine and 35.0 g of phenyl chlorothionocarbonate in 300 ml of acetonitrile is refluxed for 10 hours. The reaction solution is concentrated under reduced pressure to remove acetonitrile. Toluene (300 ml) is added to the residue and filtered to remove insoluble substance. The filtrate is concentrated under reduced pressure and purified by silica gel column-chromatography (eluent: ethyl acetate:hexane =1:1). 4,6-Dimethoxy-2-isothiocyanatopyrimidine (17.0 g) is obtained from the first eluate. mp 85°~86° C.

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. customto remove acetonitrile
  3. additionToluene (300 ml) is added to the residue
  4. filtrationfiltered
  5. customto remove insoluble substance
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. custompurified by silica gel column-chromatography (eluent: ethyl acetate:hexane =1:1)

Sources & evidence

ORD record
ord-af1813f5d4054331afb5433f76507d3a
Source dataset
uspto-grants-1990_01
Patent number
US04897105

Linked notes

Loading…