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

HRID 2351241Notes

Reaction equation

HRID 2351241 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

Conditions

Temperature
140 °C

Procedure

To 50 ml of xylene are added 15.0 g of 4-methoxy-6- methyl-2-trimethylsilylamino-1,3,5-triazine and 12.2 g of phenyl chlorothionocarbonate. The mixture is stirred at about 140° C. for 6.5 hours. After cooling the reaction mixture to room temperature, insoluble matters are filtered, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent, ethyl acetate:toluene=1:3) to yield 3.0 g of the title compound as an oil.

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. filtrationinsoluble matters are filtered
  3. concentrationthe 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-10a79d03bc7a4b8384defdea7e250c0f
Source dataset
uspto-grants-1989_10
Patent number
US04872901

Reaction notes

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