Methanesulfonic Acid → HCID 11632286, compound

HRID 2197633Notes

Reaction equation

HRID 2197633 reaction equation
I([O-])(=O)(=O)=O.[Na+].[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.CS(O)(=O)=[O:35].C(=O)(O)[O-].[Na+]>O>[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:35])=[CH:19][CH:18]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 23667635Sodium periodate2×HCID 66731247HCID 66731247, compound

Product 1

HCID 11632286HCID 11632286, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium periodate (43 mg) was added to a solution of 4-[4-(phenethylamino-methyl)-phenylsulfanyl]-benzamide (73 mg, 0.2 mmol), water (10 mL), and methane sulfonic acid (39 mg, 0.4 mmol) while stirring at room temperature. After 1 and 2 hours, and an additional equivalent of sodium periodate (43 mg) and continue to stir at room temperature. Pour the reaction into saturated aqueous sodium bicarbonate solution then extract with ethyl acetate (3×50 mL). The combined ethyl acetate extracts were dried over sodium chloride/magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield the crude product (60 mg). The crude product was purified by flash column chromatography on silica gel eluting with 10% aqueous ammonium hydroxide in ethanol and chloroform to yield 4-[4-(Phenethylamino-methyl)-benzenesulfinyl]-benzamide (26 mg): 1H NMR (DMSO-D6, 300.00 MHz): 8.98 (d, 1H, J=1.3 Hz), 8.46 (dd, 1H, J=7.9, 2.2 Hz), 8.23 (s, 1H), 8.09 (d, 1H, J=8.3 Hz), 7.75-7.66 (m, 4H), 7.49 (d, 2H, J=8.3 Hz), 7.30-7.15 (m, 5H), 3.76 (s, 2H), 2.75-2.70 (m, 4H); m/z=380.04 (M+1); HPLC=100%@5.67 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. customAfter 1 and 2 hours
  2. stirringto stir at room temperature
  3. additionPour
  4. extractionthen extract with ethyl acetate (3×50 mL)
  5. dry with materialThe combined ethyl acetate extracts were dried over sodium chloride/magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator
  8. customto yield the crude product (60 mg)
  9. customThe crude product was purified by flash column chromatography on silica gel eluting with 10% aqueous ammonium hydroxide in ethanol and chloroform

Sources & evidence

ORD record
ord-956c558cee8a4a2c968dd5009b1128bd
Source dataset
uspto-grants-2012_12
Patent number
US08338611B2

Reaction notes

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