Dichloromethane → HCID 12874990, compound

HRID 444599Notes

Reaction equation

HRID 444599 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[S:9][C:8]([S:10](NN)(=[O:12])=[O:11])=[CH:7][CH:6]=1.[Br:15]Br>CCCCCC>[Cl:4][C:5]1[S:9][C:8]([S:10]([Br:15])(=[O:12])=[O:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24408BromineHCID 12413005-chlorothiophene-2-sulfonohydrazide

Product 1

HCID 12874990HCID 12874990, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
2 °C

Procedure

In a 1-liter, three-neck flask equipped with a magnetic stirrer, a thermometer, an an addition funnel were placed 300 ml of methylene chloride, 10.63 g (0.05 mol) of 5-chloro-2-thiophenesulfonyl hydrazine, and some crushed ice. The slurry was allowed to cool to 2° C., and 16.0 g (0.10 mol) of bromine was added dropwise with stirring at such a rate that the temperature did not exceed 10° C. After the addition was complete, the methylene chloride layer was separated, dried and the methylene chloride removed in vacuo, leaving a yellow-orange oil. The oil was dissolved in hexane and the resulting solution cooled to give 6.56 g of the title compound as slightly yellow crystals, mp 35°-37°.

Workup

  1. customIn a 1-liter, three-neck flask equipped with a magnetic stirrer
  2. customdid not exceed 10° C
  3. additionAfter the addition
  4. customthe methylene chloride layer was separated
  5. customdried
  6. customthe methylene chloride removed in vacuo
  7. customleaving a yellow-orange oil
  8. temperaturethe resulting solution cooled

Sources & evidence

ORD record
ord-b1509a19944d488ba56177db47510edb
Source dataset
uspto-grants-1981_04
Patent number
US04264774

Reaction notes

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