Oxalyl chloride → 4-cyclohexyl-N-(1,1-dimethylethyl)-N-hydroxy-cyclohexane-carboxamide

HRID 477964

반응식

HRID 477964 반응식
[CH:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.Cl.[CH3:23][C:24]([NH:27][OH:28])([CH3:26])[CH3:25]>O1CCCC1.CN(C)C=O.[OH-].[Na+]>[CH:1]1([CH:7]2[CH2:8][CH2:9][CH:10]([C:13]([N:27]([C:24]([CH3:26])([CH3:25])[CH3:23])[OH:28])=[O:15])[CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

7

반응물 3

HCID 65578Oxalyl chlorideHCID 2777896N-tert-butylhydroxylamine hydrochlorideHCID 3062287(1,1'-Bi(cyclohexane))-4-carboxylic acid

생성물 1

HCID 147228684-cyclohexyl-N-(1,1-dimethylethyl)-N-hydroxy-cyclohexane-carboxamide수율 9.4%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

실험 절차

To a solution of 4-cyclohexyl-cyclohexanecarboxylic acid (1.47 g, 7 mmol) in 20 ml of tetrahydrofuran was added oxalyl chloride (0.67 ml, 7.7 mmol) and a few drops of dimethylformamide. After stirring for one hour, the reaction mixture was added dropwise into a cold (~0° C.), stirred solution of N-(1,1-dimethylethyl)hydroxylamine hydrochloride (1.75 g, 14 mmol) in 40 ml of 1N sodium hydroxide. The mixture was stirred for two hours, from 0° C. to room temperature and extracted three times with ethyl acetate. The combined ethyl acetate extracts were then washed twice with water, dried with anhydrous sodium sulfate and concentrated. Purification by flash chromatography provided 0.186 g of the 4-cyclohexyl-N-(1,1-dimethylethyl)-N-hydroxy-cyclohexane-carboxamide as a white solid (m.p. 119°-120° C.).

후처리

  1. additionthe reaction mixture was added dropwise into a cold (~0° C.)
  2. stirringThe mixture was stirred for two hours, from 0° C. to room temperature
  3. extractionextracted three times with ethyl acetate
  4. washThe combined ethyl acetate extracts were then washed twice with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-81dccbcadc124a5a82208d0bc9af450a
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04889874

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