Sodium ethanethiolate → HCID 24984324, compound

HRID 503932Notes

Reaction equation

HRID 503932 reaction equation
C([S-])C.[Na+].C[O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23]3)=[C:18]([CH3:28])[CH:17]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1>CN(C=O)C>[CH3:28][C:18]1[CH:17]=[C:16]([S:13]([C:10]2[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=2)(=[O:15])=[O:14])[CH:21]=[CH:20][C:19]=1[CH:22]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23]1

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 59428351HCID 59428351, compound

Product 1

HCID 24984324HCID 24984324, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium ethanethiolate (94 mg, 1.111 mmol) was added to a solution of 3-[4-(4-methoxy-benzenesulfonyl)-2-methyl-phenyl]-1-methyl-pyrrolidine (128 mg, 0.3705 mol) in DMF (2 mL) and the reaction mixture was heated at 100° C. for 4 hours. The solvent was evaporated under reduced pressure and the residue was purified via flash chromatography (DCM/MeOH/NH4OH) to give 4-[3-methyl-4-(1-methyl-pyrrolidin-3-yl)-benzenesulfonyl]-phenol as a white foam. The free amine was transformed in the corresponding hydrochloride (white foam) by addition of a small excess of HCl in 1,4-dioxane: MP=186.0-187.5° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-56182dbfd65f4ad68cb24cfe0e371e7c
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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