tert-Butyl carbazate → Tert-butyl 2-(benzothiazol-6-ylcarbonyl)hydrazinecarboxylate

HRID 452586

反応式

HRID 452586 の反応式
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[NH:14][NH2:15].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[S:1]1[C:5]2[CH:6]=[C:7]([C:10]([NH:15][NH:14][C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

参加物

7

反応物 4

HCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 601670Benzothiazole-6-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 68663659Tert-butyl 2-(benzothiazol-6-ylcarbonyl)hydrazinecarboxylate収率 75.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of benzothiazole-6-carboxylic acid (4.48 g, 25.0 mmol), tert-butyl carbazate (3.63 g, 27.5 mmol), 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (5.75 g, 30.0 mmol) and 1-hydroxybenzotriazole (4.05 g, 30.0 mmol) in N,N-dimethylformamide (50 mL) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/tetrahydrofuran=2/1), and crystallized from hexane/acetone to give the title compound (5.51 g, yield 75%) as colorless crystals.

後処理

  1. washwashed twice with water and once with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/tetrahydrofuran=2/1)
  5. customcrystallized from hexane/acetone

出典と根拠

ORDレコード
ord-45370c378ca6432ca518cd20c6df846b
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

関連ノート

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