Dimethyl Sulfate → Methyl 2-chloro-6-fluorobenzthioimidate

HRID 2269660Notes

Reaction equation

HRID 2269660 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](=[S:6])[NH2:5].[CH3:12]OS(OC)(=O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([S:6][CH3:12])=[NH:5]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 77452422-Chloro-6-fluorobenzene-1-carbothioamide

Product 1

HCID 11171711Methyl 2-chloro-6-fluorobenzthioimidateYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 25-mL three-necked round bottom flask equipped with a magnetic stirrer was added 2-chloro-6-fluorobenzthioamide (1.89 g, 10.0 mmol) and toluene (10 mL). Dimethylsulfate was added dropwise and the mixture was allowed to stir at reflux using a Dean Stark trap. The solids were removed via filtration and washed with small portions of toluene to give methyl 2-chloro-6-fluorobenzthioimidate as a light yellow solid: 2.7 g (87% yield): 1H NMR (DMSO-d6) δ7.7 (m, 1H), 7.5 (m, 2H), 3.3 (s, 3H), 2.7 (s, 3H); 98% pure by HPLC analysis.

Workup

  1. customInto a 25-mL three-necked round bottom flask equipped with a magnetic stirrer
  2. temperatureat reflux
  3. customThe solids were removed via filtration
  4. washwashed with small portions of toluene

Sources & evidence

ORD record
ord-55fb770f5e5144e88630ef3b1e3b4cc6
Source dataset
uspto-grants-2001_12
Patent number
US06329528B1

Reaction notes

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