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

HRID 356945

反応式

HRID 356945 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 21187831Methyl 4-(methylsulfanyl)-3-nitrobenzenecarboxylate収率 62.7%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4374b5e7f1844a5da42b094d9d49608d
出典データセット
uspto-grants-1998_11
特許番号
US05840724

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