Hydrochloric Acid → HCID 11581984, compound

HRID 2197632Notes

Reaction equation

HRID 2197632 reaction equation
[OH:1]OS([O-])=O.[K+].[CH2:7]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[O:29])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.S(=O)(O)[O-].[Na+].[OH2:39]>O1CCCC1>[CH2:7]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([C:24]2[CH:25]=[CH:26][C:27]([C:28]([NH2:30])=[O:29])=[CH:31][CH:32]=2)(=[O:1])=[O:39])=[CH:19][CH:18]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665763Sodium BisulfiteHCID 23707502Potassium hydroxy sulfiteHCID 66731247HCID 66731247, compound

Product 1

HCID 11581984HCID 11581984, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of oxone (0.18 g, 0.29 mmol) in water (2 mL) was added to a solution of 4-[4-(phenethylamino-methyl)-phenylsulfanyl]-benzamide (50 mg, 0.14 mmol), 1N aqueous hydrochloric acid (0.14 mL), and tetrahydrofuran (2 mL) at room temperature. Stir overnight at room temperature, pour into saturated aqueous sodium bisulfite, and then extract with ethyl acetate (3×50 mL). The combined ethyl acetate extracts were washed with saturated aqueous sodium bicarbonate solution, water, and brine then dried over sodium chloride/magnesium sulfate. Filter, and concentrate on a rotary evaporator to yield 100 mg of the crude product. The crude product is purified by flash column chromatography on silica gel eluting with (0.2% conc. ammonium hydroxide/2% ethanol) to (2% conc. ammonium hydroxide/20% ethanol) in chloroform to yield 4-[4-(Phenethylamino-methyl)-benzenesulfonyl]-benzamide, (15 mg): 1H NMR (DMSO-D6, 300.00 MHz): 9.06-9.01 (m, 1H), 8.50 (dd, 1H, J=8.1, 2.1 Hz), 8.31 (dd, 2H, J=8.2, 0.7 Hz), 7.96-7.81 (m, 3H), 7.61 (d, 2H, J=8.2 Hz), 7.32-7.15 (m, 6H), 3.88-3.82 (m, 2H), 2.78-2.71 (m, 4H); m/z=396.03 (M+1); HPLC=90%@5.81 minutes (5/95 to 95/5 ACN/(0.1% TFA in water) over 10 minutes, Zorbax SB-Phenyl 4.6 mm×15 cm×5 micron, λ=254 nM.

Workup

  1. extractionextract with ethyl acetate (3×50 mL)
  2. washThe combined ethyl acetate extracts were washed with saturated aqueous sodium bicarbonate solution, water, and brine
  3. dry with materialthen dried over sodium chloride/magnesium sulfate
  4. filtrationFilter
  5. concentrationconcentrate on a rotary evaporator
  6. customto yield 100 mg of the crude product
  7. customThe crude product is purified by flash column chromatography on silica gel eluting with (0.2% conc. ammonium hydroxide/2% ethanol) to (2% conc. ammonium hydroxide/20% ethanol) in chloroform

Sources & evidence

ORD record
ord-af5cc6e64f224bdbb2bb69dcf0f2cadf
Source dataset
uspto-grants-2012_12
Patent number
US08338611B2

Reaction notes

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