2-Chloro-4-(trifluoromethyl)benzenesulfonyl chloride → N-[3-Acetyl-5-chloro-4-(5-chloro-benzothiazol-2-ylsulfanyl)-phenyl]-2-chloro-4-trifluoromethyl-benzenesulfonamide

HRID 1835548Notes

Reaction equation

HRID 1835548 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([Cl:22])[C:5]([S:11][C:12]2[S:13][C:14]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:15]=3[N:16]=2)=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[Cl:23][C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1[S:34](Cl)(=[O:36])=[O:35]>N1C=CC=CC=1>[C:8]([C:6]1[CH:7]=[C:2]([NH:1][S:34]([C:25]2[CH:26]=[CH:27][C:28]([C:30]([F:31])([F:32])[F:33])=[CH:29][C:24]=2[Cl:23])(=[O:36])=[O:35])[CH:3]=[C:4]([Cl:22])[C:5]=1[S:11][C:12]1[S:13][C:14]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:15]=2[N:16]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 27366752-Chloro-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 221489061-[5-Amino-3-chloro2-(5-chloro-benzothiazol-2-ylsulfanyl)-phenyl]-ethanone2×

Product 1

HCID 22148793N-[3-Acetyl-5-chloro-4-(5-chloro-benzothiazol-2-ylsulfanyl)-phenyl]-2-chloro-4-trifluoromethyl-benzenesulfonamideYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

To a 1M solution of 1-[5-Amino-3-chloro-2-(5-chloro-benzothiazol-2-ylsulfanyl)-phenyl]-ethanone, (265) (4.12 g, 11.19 mmol) in pyridine, obtained from Aldrich, was added 2-chloro-4-trifluoromethyl-benzenesulfonyl chloride (3.75 g, 13.43 mmol) and heated to 90° C. for 1.5 hours. The crude reaction mixture was concentrated under vacuum, partitioned between 2M aqueous HCl (100 mL) and EtOAc (100 mL), and extracted 3 times with EtOAc (100 mL). The combined organic layers were washed twice with saturated aqueous brine (100 mL), dried over Na2SO4, concentrated under vacuum, purified by column chromatography (0-5% Et2O in CH2Cl2), and triturated with CH2Cl2/hexane mixture with 0.5 mL of MeOH added to yield compound 277 (4.9 g, 72%) as an off white solid.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under vacuum
  3. custompartitioned between 2M aqueous HCl (100 mL) and EtOAc (100 mL)
  4. extractionextracted 3 times with EtOAc (100 mL)
  5. washThe combined organic layers were washed twice with saturated aqueous brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. custompurified by column chromatography (0-5% Et2O in CH2Cl2)
  9. customtriturated with CH2Cl2/hexane mixture with 0.5 mL of MeOH
  10. additionadded

Sources & evidence

ORD record
ord-5929d6939ba349f5ace1eae31df28ebf
Source dataset
uspto-grants-2004_08
Patent number
US06770648B2

Reaction notes

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