4-tert-Butylcyclohexanone → tert-butyl N-[(4-tert-butylcyclohexylidene)amino]carbamate

HRID 2218967

반응식

HRID 2218967 반응식
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[NH2:13].[O-]S([O-])(=O)=O.[Mg+2].[O-]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.CC#N>[C:17]([O:16][C:14]([NH:12][N:13]=[C:8]1[CH2:9][CH2:10][CH:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

참가 물질

6

반응물 3

HCID 73924-tert-ButylcyclohexanoneHCID 70091tert-Butyl carbazateHCID 13828231HCID 13828231, 화합물

생성물 1

HCID 288080tert-butyl N-[(4-tert-butylcyclohexylidene)amino]carbamate수율 98.7%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-tert-butylcyclohexanone (3.95 g, 25.6 mmol) in CH2Cl2 (50 mL) was added tert-butyl hydrazinecarboxylate (3.83 g, 25.6 mmol). A 1:1 mixture of MgSO4/Na2SO4 was added to the reaction to make a slurry and the reaction was stirred vigorously. After 18 h, the reaction was diluted with CH3CN and filtered. The solvent was removed from the filtrate under reduced pressure to give 6.78 g of N′-(4-tert-butyl-cyclohexylidene)-hydrazinecarboxylic acid tert-butyl ester as a white foam. This material was used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) δ 9.51 (s, 1H), 2.93 (d, J=15 Hz, 1H), 2.30 (d, J=13 Hz, 1H), 2.08 (m, 1H), 1.89 (m, 2H), 1.66 (m, 1H), 1.43 (s, 9H), 1.25 (m, 1H), 1.13 (m, 1H), 1.03 (m, 1H), 0.85 (s, 9H).

후처리

  1. additionwas added to the reaction
  2. filtrationfiltered
  3. customThe solvent was removed from the filtrate under reduced pressure

출처 및 근거

ORD 기록
ord-567a1aff1b3b4d1c8fe24a80795ebd27
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07414040B2

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