Triethylamine → N-cyclohexyl-2,4-dimethylfuran-3-hydroxamic acid

HRID 1730812

反応式

HRID 1730812 の反応式
C(N(CC)CC)C.Cl.[CH:9]1([NH:15][OH:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[CH3:17][C:18]1[O:19][CH:20]=[C:21]([CH3:26])[C:22]=1[C:23](Cl)=[O:24]>C1C=CC=CC=1>[CH:9]1([N:15]([C:23]([C:22]2[C:21]([CH3:26])=[CH:20][O:19][C:18]=2[CH3:17])=[O:24])[OH:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 3084432N-Cyclohexylhydroxylamine hydrochlorideHCID 130199852,4-Dimethyl-3-furoyl chloride

生成物 1

HCID 21496533N-cyclohexyl-2,4-dimethylfuran-3-hydroxamic acid

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

30 Parts of triethylamine is added to a suspension of 25 parts of N-cyclohexylhydroxylamine hydrochloride in 480 parts of benzene. After the mixture has been stirred for 1 hour, 20 parts of 2,4-dimethylfuran-3-carboxylic chloride is dripped in at room temperature. After the mixture has been stirred for a further 2 hours it is suction filtered, the residue is washed with benzene and the combined benzene phases are washed with water, dried with anhydrous sodium sulfate and evaporated. There is obtained 34 parts of N-cyclohexyl-2,4-dimethylfuran-3-hydroxamic acid in the form of an oil. This oil is dissolved in 370 parts of dichloromethane; at room temperature and while stirring, 18 parts of sodium hydroxide in 70 parts of water, and 28 parts of dimethyl sulfate are added to the solution. After the mixture has been stirred for 1 hour the organic phase is separated, washed with water, dried with sodium sulfate, evaporated and chromatographed using silica gel with a mixture of equal portions of ethyl acetate and cyclohexane. When the eluate is evaporated there is obtained 32 parts of O-methyl-N-cyclohexyl-2,4-dimethylfuran-3-hydroxamic acid having a boiling point at 0.01 mm Hg of 122° to 124° C and the refractive index nD25 : 1.5010. ##SPC13##

後処理

  1. customis dripped in at room temperature
  2. stirringAfter the mixture has been stirred for a further 2 hours it
  3. filtrationfiltered
  4. washthe residue is washed with benzene
  5. washthe combined benzene phases are washed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customevaporated

出典と根拠

ORDレコード
ord-d7ff2d4355894f3cb238b7841a40b25e
出典データセット
uspto-grants-1976_11
特許番号
US03993772

関連ノート

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