Water → HCID 178499017, compound

HRID 329576Notes

Reaction equation

HRID 329576 reaction equation
[C:1]([NH:4][C:5]1[NH:9][N:8]=[C:7](CC2C=CC=CC=2)[C:6]=1[C:17]([O:19][CH3:20])=S)(=[O:3])[CH3:2].[OH2:21].[S:22]([Cl:26])(Cl)(=[O:24])=[O:23]>C(Cl)Cl>[C:1]([NH:4][C:5]1[NH:9][N:8]=[C:7]([S:22]([Cl:26])(=[O:24])=[O:23])[C:6]=1[C:17]([O:19][CH3:20])=[O:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 178502586HCID 178502586, compound

Product 1

HCID 178499017HCID 178499017, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

73.0 g (239 mmol) Methyl 5-acetamido-3-benzylthiopyrazole-4-carboxylate was dissolved in 470 ml methylene chloride and treated with 124.15 g silica gel and 25.6 g water and cooled to 0° C. 160.6 g (1.19 mol) Sulphuryl chloride in 730 ml methylene chloride was added dropwise. The mixture was stirred for 3 hours at 0° C., filtered, washed several times with methylene chloride, dried over magnesium sulphate and concentrated. The residue was triturated with ether/hexane, the crystals suction filtered, washed with hexane and dried.

Workup

  1. filtrationfiltered
  2. washwashed several times with methylene chloride
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was triturated with ether/hexane
  6. filtrationthe crystals suction filtered
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-91d4d5b1483b436284fbda1524532359
Source dataset
uspto-grants-1990_01
Patent number
US04892576

Reaction notes

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