Sulfuryl chloride → 2-Chloromethylthio-5-chloropyrimidine

HRID 905211Notes

Reaction equation

HRID 905211 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([Cl:9])=[CH:5][N:4]=1.S(Cl)([Cl:13])(=O)=O>ClCCl>[Cl:13][CH2:1][S:2][C:3]1[N:8]=[CH:7][C:6]([Cl:9])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 47370635-Chloro-2-(methylthio)pyrimidine

Product 1

HCID 134351352-Chloromethylthio-5-chloropyrimidineYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methylthio-5-chloropyrimidine (75 mmol) and sulfuryl chloride (104 mmol) were heated together in refluxing dichloromethane (100 ml) for 3 h. Evaporation of the mixture left a solid which was recrystallized from ethanol; yield 82%, m.p. 78° C. 1H NMR (CDCl3): 5.20 (SCH2), 8.54 (H-4, H-6).

Workup

  1. customEvaporation of the mixture
  2. waitleft a solid which
  3. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-c3f5d4f3ef07438dbbc7a0e9cd2071ca
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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