Methanol → HCID 22036190, compound

HRID 1789665Notes

Reaction equation

HRID 1789665 reaction equation
[CH2:1]([O:3][C:4]1[CH:25]=[CH:24][C:7]([CH2:8][N:9]([C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=2)[CH2:10][C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)=[CH:6][CH:5]=1)[CH3:2].OOS([O-])=O.[K+].[OH2:32].C[OH:34]>>[CH2:1]([O:3][C:4]1[CH:25]=[CH:24][C:7]([CH2:8][N:9]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:23])(=[O:34])=[O:32])=[CH:20][CH:21]=2)[CH2:10][C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 22036166HCID 22036166, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22036190HCID 22036190, compoundYield 92%

Procedure

To 241 mg (0.652 mmol) of (4-Ethoxy-benzyl)-(4-methylsulfanyl-phenyl)-thiophen-3-ylmethyl-amine dissolved in 6 mL methanol was added 800 mg (1.3 mmol) OXONE™ followed by 600 μL water. The mixture was stirred at room temperature for 2 h, then partitioned between EtOAc and water, adding 1 N NaOH until the aqueous phase was neutral. The organic layer was then dried over MgSO4 and concentrated. (4-Ethoxy-benzyl)-(4-methanesulfonyl-phenyl)-thiophen-3-ylmethyl-amine was obtained in 92% yield (240 mg) and appeared pure by 1H NMR.

Workup

  1. custompartitioned between EtOAc and water
  2. additionadding 1 N NaOH until the aqueous phase
  3. dry with materialThe organic layer was then dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b33edf77ccf241e9a56e7b20cf2ad78e
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

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