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

HRID 452586

반응식

HRID 452586 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-45370c378ca6432ca518cd20c6df846b
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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