Water → Methyl 1-methyl-3-(3-bromophenyl)-4-chloropyrazole-5-carboxylate

HRID 2412926Notes

Reaction equation

HRID 2412926 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[CH:12]=2)=[N:3]1.S(Cl)([Cl:21])(=O)=O.O>C1C=CC=CC=1>[CH3:1][N:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([Cl:21])[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[CH:12]=2)=[N:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 13370531HCID 13370531, compound

Product 1

HCID 13370534Methyl 1-methyl-3-(3-bromophenyl)-4-chloropyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A reaction mixture was prepared from 13.5 g. of methyl 1-methyl-3-(3-bromophenyl)pyrazole-5-carboxylate and 6.2 g. of sulfuryl chloride in benzene solution. The reaction mixture was heated to refluxing temperature for about 36 hours, and was then cooled and poured into water. The aqueous mixture was extracted with ethyl acetate, and the ethyl acetate extract separated and dried. Removal of the ethyl acetate in vacuo yielded, as a residue, methyl 1-methyl-3-(3-bromophenyl)-4-chloropyrazole-5-carboxylate formed in the above reaction. Recrystallization of the residue from hexane yielded crystalline material melting at 91°-3° C.

Workup

  1. customA reaction mixture was prepared from 13.5 g
  2. temperatureThe reaction mixture was heated
  3. temperatureto refluxing temperature for about 36 hours
  4. temperaturewas then cooled
  5. extractionThe aqueous mixture was extracted with ethyl acetate
  6. extractionthe ethyl acetate extract
  7. customseparated
  8. customdried
  9. customRemoval of the ethyl acetate in vacuo
  10. customyielded, as a residue

Sources & evidence

ORD record
ord-b63dc983b38846d48f43eeaf6bfffb1c
Source dataset
uspto-grants-1985_01
Patent number
US04495195

Reaction notes

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