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

HRID 2218967

反応式

HRID 2218967 の反応式
[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]

参加物

6

反応物 3

HCID 73924-tert-ButylcyclohexanoneHCID 70091tert-Butyl carbazateHCID 13828231HCID 13828231、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-567a1aff1b3b4d1c8fe24a80795ebd27
出典データセット
uspto-grants-2008_08
特許番号
US07414040B2

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