Dimethylformamide → HCID 22998443, compound

HRID 2271013Notes

Reaction equation

HRID 2271013 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([S:14]([O-])(=[O:16])=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Na+].CN(C=O)C.S(Cl)([Cl:28])=O>>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([S:14]([Cl:28])(=[O:16])=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 23664902HCID 23664902, compound

Product 1

HCID 22998443HCID 22998443, compound

Conditions

Temperature
50 °C

Procedure

A mixture of sodium 5-(4-trifluoromethylphenyl)thiophene sulfonate (1.50 g) and DMF (498 mg) in thionyl chloride (7.5 ml) was stirred for 2 hours at 50° C. The mixture was concentrated and partitioned between AcOEt and 3% aqueous sodium bicarbonate. The organic layer was separated, washed with 3% aqueous NaHCO3 solution and brine, dried over sodium sulfate and evaporated in vacuo after filtration to give 1.39 g of 5-(4-trifluoromethylphenyl)thiophene-2-sulfonylchloride as a solid.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between AcOEt and 3% aqueous sodium bicarbonate
  3. customThe organic layer was separated
  4. washwashed with 3% aqueous NaHCO3 solution and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. filtrationafter filtration

Sources & evidence

ORD record
ord-f67d8b7b86404cb68b035e64c4c49909
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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