Phenyl thioxochloroformate → 2-Isothiocyanato-4-methoxy-6-methyl-1,3,5-triazine

HRID 330448Notes

Reaction equation

HRID 330448 reaction equation
[CH3:1][O:2][C:3]1[N: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(C)=CC=CC=1>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([N:10]=[C:22]=[S:23])[N:4]=1

Participants

4

Reactant 2

HCID 70498Phenyl thioxochloroformateHCID 13587633HCID 13587633, compound

Product 1

HCID 142756812-Isothiocyanato-4-methoxy-6-methyl-1,3,5-triazineYield 23.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 15.0 g of 4-methoxy-6-methyl-2-trimethylsilylamino-1,3,5-triazine and 12.2 g of phenyl chlorothionocarbonate in 50 ml of xylene is stirred for 6.5 hours at ca. 140° C. The reaction solution is cooled to room temperature, and filtered to remove insoluble substance, and the resulting filtrate is concentrated under reduced pressure. The residue is purified by silica gel column-chromatography (eluent: ethyl acetate:toluene =1:3) to give 3.0 g of the title compound as an oil.

Workup

  1. filtrationfiltered
  2. customto remove insoluble substance
  3. concentrationthe resulting filtrate is concentrated under reduced pressure
  4. customThe residue is purified by silica gel column-chromatography (eluent: ethyl acetate:toluene =1:3)

Sources & evidence

ORD record
ord-98758965c70d4c33a23c627ee429ba61
Source dataset
uspto-grants-1990_01
Patent number
US04897105

Reaction notes

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