Benzyl mercaptan → 4-(Benzyloxy)-2-(benzylthio)-1-nitrobenzene

HRID 601277Notes

Reaction equation

HRID 601277 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11](F)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:25]([SH:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([S:32][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 10340Sodium CarbonateHCID 221807044-Benzyloxy-2-fluoro-1-nitrobenzene

Product 1

HCID 670634434-(Benzyloxy)-2-(benzylthio)-1-nitrobenzeneYield 100.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A slurry of the product of Example 304A (15 g, 0.061 mol) in ethanol (100 mL), was treated with sodium carbonate (6.41 g, 0.061 mol) and benzyl mercaptan (7.5 mL, 0.058 mol) in water (50 mL). The reaction mixture was refluxed for 5 hours, cooled to 25° C. and poured into of distilled water (800 mL). The resulting slurry was stirred forl hour at 25° C. and filtered. The resulting yellow solid was washed with water and dried in a vacuum oven at 50° C. to give the title compound (20.53 g). 1H NMR (300 MHz, DMSO-d6) δ ppm 4.35 (s, 2 H) 5.27 (s, 2 H) 7.02 (dd, J=9.19, 2.57 Hz, 1 H) 7.16 (d, J=2.57 Hz, 1 H) 7.40 (m, 10 H) 8.24 (d, J=9.19 Hz, 1 H). ESI m/z (M+H)+: 352

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. filtrationfiltered
  3. washThe resulting yellow solid was washed with water
  4. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-4fce084d907f47cc98076dbc63873733
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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