tert-Butyl mercaptan → Methyl 3-[(tert-butylthio)diazenyl]-4-fluoro-2-methylbenzoate

HRID 1639803노트

반응식

HRID 1639803 반응식
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([O:7][CH3:8])=[O:6].[N:14]([O-])=O.[Na+].C([O-])(=O)C.[K+].[CH3:23][C:24]([SH:27])([CH3:26])[CH3:25]>Cl.O.C(O)C>[C:24]([S:27][N:14]=[N:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([O:7][CH3:8])=[O:6])([CH3:26])([CH3:25])[CH3:23]

참가 물질

8

반응물 4

HCID 6387tert-Butyl mercaptanHCID 517044Potassium AcetateHCID 23668193Sodium NitriteHCID 59334547Methyl 3-amino-4-fluoro-2-methylbenzoate

생성물 1

HCID 86641924Methyl 3-[(tert-butylthio)diazenyl]-4-fluoro-2-methylbenzoate수율 62.2%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of methyl 3-amino-4-fluoro-2-methylbenzoate (3.00 g, 16.4 mmol) in hydrochloric acid (6 N, 54.6 mL) was added a solution of sodium nitrite (1.24 g, 18.0 mmol) in water (3 mL) at 0° C., and the mixture was stirred for 2 hr. To the reaction solution was added aqueous potassium acetate solution (30%) at 0° C. to adjust the reaction solution to pH 4, and a solution of 2-methylpropane-2-thiol (2.03 mL, 18.0 mmol) in ethanol (3 mL) was added. The reaction solution was stirred at room temperature for 12 hr, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give methyl 3-[(tert-butylthio)diazenyl]-4-fluoro-2-methylbenzoate (2.90 g, yield 62%) as a crudely purified product.

후처리

  1. stirringThe reaction solution was stirred at room temperature for 12 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-75e798ba64614d9f80a6f1a8517a7086
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110585B2

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