Benzyl mercaptan → HCID 13322001, compound

HRID 325586Notes

Reaction equation

HRID 325586 reaction equation
C[O-].[Na+].[CH2:4]([SH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:12][S:13]([C:16]1[S:17][CH:18]=[CH:19][C:20]=1Br)(=[O:15])=[O:14]>CN(C)C=O>[CH3:12][S:13]([C:16]1[S:17][CH:18]=[CH:19][C:20]=1[S:11][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 10942334Sodium MethoxideHCID 13322000HCID 13322000, compound

Product 1

HCID 13322001HCID 13322001, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 g of sodium methoxide in 100 ml of dimethylformamide was added 6 ml of benzyl mercaptan followed by 10 g of 3-bromo-2-thienyl methyl sulfone. The temperature rose to 70°. The mixture was stirred at room temperature for 16 hours and then at 70° for 1 hour. Most of the dimethylformamide was evaporated at reduced pressure and ice-water was added to the residue. The resulting solid was filtered, washed with ice-water and hexane to afford 14 g of crude XXVII. A dried sample of this material had m.p. 95°-97° and peak at 4.2 in the NMR spectrum (CDCl3), consistent with an aromatic benzyl sulfide.

Workup

  1. customrose to 70°
  2. waitat 70° for 1 hour
  3. customMost of the dimethylformamide was evaporated at reduced pressure and ice-water
  4. additionwas added to the residue
  5. filtrationThe resulting solid was filtered
  6. washwashed with ice-water and hexane

Sources & evidence

ORD record
ord-8d227581421940dd98fba372a29926ef
Source dataset
uspto-grants-1984_04
Patent number
US04441910

Reaction notes

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