Sulfuryl chloride → HCID 58674500, compound

HRID 1994100Notes

Reaction equation

HRID 1994100 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].S(Cl)([Cl:27])(=O)=O>ClCCCl.CCOC(C)=O>[Cl:27][C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:20]([F:21])([F:22])[F:23])[CH:4]=2)=[O:19])[CH:17]=[CH:16][C:15]=1[OH:18]

Participants

5

Reactant 2

HCID 24648Sulfuryl chloride2×HCID 51355180HCID 51355180, compound

Product 1

HCID 58674500HCID 58674500, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
84 °C

Procedure

To a solution of N-[4-chloro-3-(trifluoromethyl)phenyl]-3-(4-hydroxyphenyl)propanamide (1.33 g, 3.89 mmol) in DCE was added sulfuryl chloride (4.28 mL, 4.28 mmol) slowly over 45 min. The reaction mixture was heated at 84° C. overnight and then additional sulfuryl chloride was added. After heating for 2 h, the reaction mixture was cooled to rt and diluted with EtOAc. The combined organic solutions were washed with water and brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give the title compound (0.66 g, 45%).

Workup

  1. temperatureAfter heating for 2 h
  2. temperaturethe reaction mixture was cooled to rt
  3. washThe combined organic solutions were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-51c65b3ee1cb48338231bd02153b7bc9
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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