Benzene → HCID 59631668, compound

HRID 2369077Notes

Reaction equation

HRID 2369077 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:17][C:16]([S:18](O)(=[O:20])=[O:19])=[CH:15][CH:14]=2)=[CH:11][C:10]([C:22]([F:25])([F:24])[F:23])=[N:9]1.C1C=CC=CC=1.S(Cl)([Cl:34])=O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:17][C:16]([S:18]([Cl:34])(=[O:20])=[O:19])=[CH:15][CH:14]=2)=[CH:11][C:10]([C:22]([F:25])([F:24])[F:23])=[N:9]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 59632973HCID 59632973, compound

Product 1

HCID 59631668HCID 59631668, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(1-(2-Chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophene-2-sulfonic acid (˜3.2 mmol from previous step) was combined with benzene (5.0 mL) in a reaction vial. This mixture was treated with thionyl chloride (5.0 mL, 69 mmol) and a catalytic amount of dimethylformamide (0.1 mL). The reaction was then heated to reflux in an oil bath. After refluxing for 1 hour the reaction mixture was concentrated under reduced pressure to afford a yellow oil that partially solidified under reduced pressure. This crude material was purified by flash column chromatography eluting with a gradient from 10% to 30% EtOAc/hexane. Product-containing fractions were collected and concentrated to afford 5-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophene-2-sulfonyl chloride as a pale yellow oil. The mostly pure material was carried on to subsequent transformations without further purification.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux in an oil bath
  3. temperatureAfter refluxing for 1 hour the reaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. customto afford a yellow oil
  6. customThis crude material was purified by flash column chromatography
  7. washeluting with a gradient from 10% to 30% EtOAc/hexane
  8. customProduct-containing fractions were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b32e7886cb1c4314b5aa3d18ff9ce407
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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