Water → 2,4-Dichloro-5-(2-((trichloromethyl)thio)phenyl)pyrimidine

HRID 711395Notes

Reaction equation

HRID 711395 reaction equation
O.[Cl:2][C:3]1[N:8]=[C:7]([Cl:9])[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]C)=[CH:5][N:4]=1.[C:18]([Cl:22])(Cl)([Cl:20])[Cl:19]>>[Cl:2][C:3]1[N:8]=[C:7]([Cl:9])[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16][C:18]([Cl:22])([Cl:20])[Cl:19])=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 1183403012,4-Dichloro-5-(2-(methylthio)phenyl)pyrimidine2×

Product 1

HCID 1183402992,4-Dichloro-5-(2-((trichloromethyl)thio)phenyl)pyrimidineYield 99%

Procedure

A 2-neck 250 mL round bottom flask was equipped with a gas inlet adapter and a gas outlet attached to two traps in series, the first trap being empty and the second trap containing water. The reaction vessel was charged with 2,4-dichloro-5-(2-(methylthio)phenyl)pyrimidine and carbon tetrachloride (49.8 ml) and heated to reflux to dissolve the 2,4-dichloro-5-(2-(methylthio)phenyl)pyrimidine, then cooled to room temperature creating a clear colorless solution. Chlorine gas was bubbled through the reaction solution while stirring vigorously creating a clear yellow solution. The reaction was monitored by direct NMR of aliquots diluted in DMSO-d6. Upon completion the reaction solution was concentrated in vacuo yielding 14.7 g (99% yield) of 2,4-dichloro-5-(2-((trichloromethyl)thio)phenyl)pyrimidine as yellow solids.

Workup

  1. customA 2-neck 250 mL round bottom flask was equipped with a gas inlet adapter and a gas outlet
  2. temperatureheated
  3. temperatureto reflux
  4. customChlorine gas was bubbled through the reaction solution
  5. additiondiluted in DMSO-d6
  6. concentrationUpon completion the reaction solution was concentrated in vacuo

Sources & evidence

ORD record
ord-7dc84110461543158b050c26b2707d6c
Source dataset
uspto-grants-2015_11
Patent number
US09181270B2

Reaction notes

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