4-(Trifluoromethyl)benzenesulfonyl chloride → HCID 18931280, compound

HRID 1598993Notes

Reaction equation

HRID 1598993 reaction equation
[NH2:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][C:5]([O:15][CH3:16])=[C:6]([C:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][Cl:13])[CH:7]=1.[F:19][C:20]([F:32])([F:31])[C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C1COCC1>[Cl:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:6]1[C:5]([O:15][CH3:16])=[CH:4][C:3]([O:17][CH3:18])=[C:2]([NH:1][S:27]([C:24]2[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:31])[F:32])=[CH:26][CH:25]=2)(=[O:29])=[O:28])[CH:7]=1)=[O:14]

Participants

4

Reactant 2

HCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 18931134HCID 18931134, compound

Product 1

HCID 18931280HCID 18931280, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1-(5-amino-2,4-dimethoxyphenyl)-5-chloro-1-pentanone (0.54 g, 2 mmol), prepared as in Example 13, 4-trifluoromethylbenzenesulfonyl chloride (0.51 g, 2.1 mmol) triethylamine (0.25 g, 2.5 mmol) and THF (approximately 50 mL) was stirred 16 hours at approximately 25° C. The mixture was concentrated and the residue was partitioned between ethyl acetate and dilute ammonium hydroxide. The organic layer was washed with water (1×) and then brine (1×), dried (K2CO3), filtered and concentrated to give N-[5-(5-chloropentanoyl)-2,4-dimethoxyphenyl]-4-trifluoromethylbenzenesulfonamide (0.8 g, 1.7 mmol), m.p. 150°-153° C.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and dilute ammonium hydroxide
  3. washThe organic layer was washed with water (1×)
  4. dry with materialbrine (1×), dried (K2CO3)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8ec4356646b0497d8721dbe661821145
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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