Water → 2,4-Dinitrobenzyl mercaptan

HRID 726420Notes

Reaction equation

HRID 726420 reaction equation
C([S:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16])(=O)C.O>S(=O)(=O)(O)O.O.CO>[N+:15]([C:7]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:6]=1[CH2:5][SH:4])([O-:17])=[O:16]

Participants

5

Reactant 2

HCID 962WaterHCID 10729733S-(2,4-dinitrobenzyl) thioacetate

Product 1

HCID 107038212,4-Dinitrobenzyl mercaptanYield 98.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21910475Sulfuric acid hydrate (1:1)Solvent

Procedure

A stirred suspension of S-(2,4-dinitrobenzyl) thioacetate 16b (8.2 g, 32 mmol) in concentrated sulfuric acid--water (1:1 v/v; 14.08 cm3) and methanol (128 cm3) was heated, under reflux, for 1.5 h. The cooled products were poured into water (300 cm3) and the resulting mixture was extracted with ether (2×400 cm3). The combined organic extracts were washed with water (300 cm3), dried (MgSO4) and evaporated under reduced pressure to give 2,4-dinitrobenzyl mercaptan 17b as a yellow oil (6.75 g, 98 %) (Found: M+ =214.0084 12 C11H614N216O432S requires: 214.0048); δH [CDCl3 ] 2.21 (1 H, t, J 8.7), 4.10 (2 H, d, J 8.7), 7.75 (1 H, d, J 8.7), 8.44 (1 H, dd, J 2.4 and 8.5), 8.77 (1 H, d, J 2.4); δC [CDCl3 ] 26.2, 121.0, 127.8, 133.0, 143.6, 146.9, 148.0.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux, for 1.5 h
  3. extractionthe resulting mixture was extracted with ether (2×400 cm3)
  4. washThe combined organic extracts were washed with water (300 cm3)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-017107b6ee7543589c1463dbaa394ed2
Source dataset
uspto-grants-1998_01
Patent number
US05708161

Reaction notes

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