Hydrochloric Acid → N-(4-biphenyl-3-yl-thiazol-2-yl)-4-methyl-benzenesulfonamide

HRID 1417284Notes

Reaction equation

HRID 1417284 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]=[C:9]([N:12](COC)[S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[S:10][CH:11]=2)[CH:2]=1.Cl.O>O1CCCC1>[C:1]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]=[C:9]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[S:10][CH:11]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 21845572N-(4-biphenyl-3-yl-thiazol-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide

Product 1

HCID 21845585N-(4-biphenyl-3-yl-thiazol-2-yl)-4-methyl-benzenesulfonamideYield 45.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.29 g of N-(4-biphenyl-3-yl-thiazol-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide in 6 ml of tetra-hydrofuran was stirred at room temperature for 6 hours after the addition of 1.5 ml of 6N hydrochloric acid. The reaction mixture was added to 40 ml of water and extracted with ethyl acetate. The organic phases were combined, dried with magnesium sulphate and concentrated. Recrystallization from 10 ml of 50% ethanol yielded 120 mg of N-(4-biphenyl-3-yl-thiazol-2-yl)-4-methyl-benzenesulfonamide as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried with magnesium sulphate
  3. concentrationconcentrated
  4. customRecrystallization from 10 ml of 50% ethanol

Sources & evidence

ORD record
ord-485f8b76b32441aead511284301b7f8c
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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