Water → HCID 58009565, compound

HRID 1009466Notes

Reaction equation

HRID 1009466 reaction equation
[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]([NH:8][S:9]([C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.O.C(O)(=O)C.O>C1COCC1>[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]([NH:8][S:9]([C:12]2[CH:20]=[CH:19][C:15]([CH2:16][OH:17])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8498138HCID 8498138, compoundHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 58009565HCID 58009565, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

652 mg of 4-{[(3-chloro-2-methylphenyl)amino]sulfonyl}benzoic acid was dissolved in 10.0 mL of THF, and 6.00 mL of a 1 M borane-THF complex was added thereto under an argon atmosphere, followed by stirring at room temperature for 4 hours. To the reaction liquid was added 1.00 mL of a mixed solution of water-acetic acid (1:1) and added water, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 467 mg of N-(3-chloro-2-methylphenyl)-4-(hydroxymethyl)benzenesulfonamide.

Workup

  1. addition6.00 mL of a 1 M borane-THF complex was added
  2. customTo the reaction liquid
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0ed9e4bcc6b345f3af7939d8ab9cb2ed
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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