Hydrochloric Acid → Ethyl 4-benzylthio-3-nitrobenzoate

HRID 2395559Notes

Reaction equation

HRID 2395559 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH2:16]([SH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.[OH-].[Li+].Cl>CN(C)C=O.CCOCC>[CH2:16]([S:23][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7509Benzyl mercaptanHCID 168937Lithium hydroxide, monohydrateHCID 1268247Ethyl 4-chloro-3-nitrobenzoate

Product 1

HCID 18989148Ethyl 4-benzylthio-3-nitrobenzoateYield 73.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-chloro-3-nitrobenzoate (10 g) and benzyl mercaptan (5.41 g) were dissolved in N,N-dimethylformamide and whilst stirring, lithium hydroxide monohydrate (1.83 g) was added. The mixture was stirred overnight then poured into ether and 2N hydrochloric acid. The organic phase was washed with water, dried over anhydrous magnesium sulphate and evaporated to yield ethyl 4-benzylthio-3-nitrobenzoate (10.16 g), obtained as an oil, NMR (CDCl3) δ1.41 (3H, t), 4.24 (2H,s), 4.40 (2H,q), 7.3-7.47 (5H), 7.53 (1H,d), 8.14 (1H,dd), 8.86 (1H,d).

Workup

  1. stirringThe mixture was stirred overnight
  2. washThe organic phase was washed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-dce8af3792ac4c548654b8e4b8242555
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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