Methyl 4-chloro-3-nitrobenzoate → Methyl 4-(methylsulfanyl)-3-nitrobenzenecarboxylate

HRID 1383500Notes

Reaction equation

HRID 1383500 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][S-:16].[Na+]>CC(C)=O>[CH3:15][S:16][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 735797Methyl 4-chloro-3-nitrobenzoateHCID 4378561Sodium methanethiolate

Product 1

HCID 21187831Methyl 4-(methylsulfanyl)-3-nitrobenzenecarboxylateYield 62.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of methyl 4-chloro-3-nitrobenzoate (28 g) in acetone (250 mL) is treated portionwise with sodium thiomethoxide (10 g) and the mixture is stirred overnight at room temperature. After filtration, the solution is concentrated and water (300 mL) is added to the residue. The yellow solid is filtered off and subjected to flash chromatography eluting with a mixture of diethyl ether and pentane (1:4 v/v), to give methyl 4-methylthio-3-nitrobenzoate (18.5 g), in the form of a yellow solid, m.p. 118-120° C.

Workup

  1. filtrationAfter filtration
  2. concentrationthe solution is concentrated
  3. additionwater (300 mL) is added to the residue
  4. filtrationThe yellow solid is filtered off
  5. washeluting with a mixture of diethyl ether and pentane (1:4 v/v)

Sources & evidence

ORD record
ord-0a65982580f94e178a71ff26e59153bf
Source dataset
uspto-grants-2001_07
Patent number
US06255326B1

Reaction notes

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