Benzyl mercaptan → HCID 14305315, compound

HRID 248292Notes

Reaction equation

HRID 248292 reaction equation
[H-].[Na+].[CH2:3]([SH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F[C:12]1[C:17]([S:18][CH2:19][CH2:20][CH3:21])=[CH:16][CH:15]=[CH:14][N:13]=1>O>[C:4]1([CH2:3][S:10][C:12]2[C:17]([S:18][CH2:19][CH2:20][CH3:21])=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 14305314HCID 14305314, compound

Product 1

HCID 14305315HCID 14305315, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 0.62 g (0.013 mol) of 50% sodium hydride (in mineral oil), which had been washed with hexanes, in 20 mls dry dimethylformamide cooled to -5° under nitrogen was added dropwise 1.6 g (0.013 mol) benzyl mercaptan such that the temperature was maintained below 5°. The suspension was stirred at room temperature for 1 hour, cooled to 0°, and a solution of 2.0 g (0.012 mol) of the product from Example 1 was added dropwise while maintaining the temperature between 0° and 5°. After warming to room temperature, the solution was poured into water and extracted with ether. The combined organic layers were washed with water and with brine, dried over magnesium sulfate, and evaporated to an oil which was purified by flash chromatography to afford 0.9 g (27%) oil: NMR (CDCl3, 200 Mhz), 1.02 (3H, t, J=7 Hz), 1.6 (2H, m), 2.9 (2H, t, J=7 Hz), 4.45 (2H, s), 6.9-7.6 (7H, m), 8.3 (1H, m); IR (neat) 1560, 1370 cm-1.

Workup

  1. washhad been washed with hexanes, in 20 mls dry dimethylformamide
  2. temperaturecooled to -5° under nitrogen
  3. temperaturewas maintained below 5°
  4. temperaturecooled to 0°
  5. temperaturewhile maintaining the temperature between 0° and 5°
  6. temperatureAfter warming to room temperature
  7. extractionextracted with ether
  8. washThe combined organic layers were washed with water and with brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated to an oil which
  11. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-ae20123c9d33416e98b11fdf85164d30
Source dataset
uspto-grants-1993_05
Patent number
US05209770

Reaction notes

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