Dimethyl Sulfate → HCID 18347930, compound

HRID 2269662Notes

Reaction equation

HRID 2269662 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].[S:12]([O:17]C)([O:15][CH3:16])(=[O:14])=[O:13]>C1(C)C=CC=CC=1>[CH3:16][O:15][S:12]([OH:17])(=[O:14])=[O:13].[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([S:6][CH3:16])=[NH:5]

Participants

4

Reactant 2

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

Product 1

HCID 18347930HCID 18347930, compoundYield 173%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

2-Chloro-6-fluorobenzthioamide (21.9 g, 0.12 mol) and dimethyl sulfate (12 mL, 16.0 g, 0.13 mol) were stirred together in 100 mL of toluene and refluxed for 2 h. The slurry was cooled to 25° C. and the white crystals collected on a glass buchner funnel and rinsed with a small quantity of acetone. After air suction drying for 1 h, 35.5 g of methyl 2-chloro-6-fluorobenzthioimidate methylsulfate salt was obtained, mp 147-151° C., representing a nominal wt. % yield of 96%.

Workup

  1. temperaturerefluxed for 2 h
  2. customthe white crystals collected on a glass buchner funnel
  3. washrinsed with a small quantity of acetone
  4. customAfter air suction drying for 1 h

Sources & evidence

ORD record
ord-1427c8f9d8374d8ab2891b600602a2a1
Source dataset
uspto-grants-2001_12
Patent number
US06329528B1

Reaction notes

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