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

HRID 356945

반응식

HRID 356945 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4374b5e7f1844a5da42b094d9d49608d
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840724

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