Hydrochloric Acid → HCID 59410236, compound

HRID 2382706Notes

Reaction equation

HRID 2382706 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][C:11]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:13]=2[C:14]#[N:15])=[CH:6][C:5]([S:20](Cl)(=[O:22])=[O:21])=[C:4]([O:24][CH3:25])[CH:3]=1.N1C=CC=CC=1.[CH3:32][NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl>ClCCl>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][C:11]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:13]=2[C:14]#[N:15])=[CH:6][C:5]([S:20]([N:33]([CH3:32])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:22])=[O:21])=[C:4]([O:24][CH3:25])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7515N-MethylanilineHCID 866435054-Chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzenesulfonyl chloride

Product 1

HCID 59410236HCID 59410236, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzenesulfonyl chloride (100 mg, 0.24 mmol) in dichloromethane (3 mL), was added pyridine (0.04 mL, 0.48 mmol), followed by addition of N-methylaniline (0.05 mL, 0.48 mmol). The mixture was stirred at r.t. for 16 hrs, then poured into 1 N HCl solution (10 mL). The product was extracted with ethyl acetate and the organic layer was washed with 1N HCl and water, then was dried over MgSO4. Concentration gave 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-N-methyl-N-phenyl-benzenesulfonamide 15-1, (108 mg). MS: 482.0 (M+H)+; tR=8.76 min (method 2).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washthe organic layer was washed with 1N HCl and water
  3. dry with materialwas dried over MgSO4
  4. concentrationConcentration

Sources & evidence

ORD record
ord-87f9b932951f4fbf90cac894d476a08c
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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