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

HRID 1639803ノート

反応式

HRID 1639803 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-75e798ba64614d9f80a6f1a8517a7086
出典データセット
uspto-grants-2012_02
特許番号
US08110585B2

反応ノート

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