Water → N-cyclohexyl-2,4,5-trimethylfuran-3-hydroxamic acid

HRID 1730810

Reaction equation

HRID 1730810 reaction equation
Cl.[CH:2]1([NH:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])O.[Na+].O.[CH3:16][C:17]1[O:18][C:19]([CH3:26])=[C:20]([CH3:25])[C:21]=1[C:22](Cl)=[O:23]>ClCCl>[CH:2]1([N:8]([C:22]([C:21]2[C:20]([CH3:25])=[C:19]([CH3:26])[O:18][C:17]=2[CH3:16])=[O:23])[OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 3084432N-Cyclohexylhydroxylamine hydrochlorideHCID 145359342,4,5-Trimethyl-3-furancarbonyl chloride

Product 1

HCID 21496536N-cyclohexyl-2,4,5-trimethylfuran-3-hydroxamic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

49 Parts of N-cyclohexylhydroxylamine hydrochloride is dissolved in 400 parts of dichloromethane; at room temperature a solution of 50.4 parts of sodium hydrogen carbonate in 500 parts of water and subsequently 51.6 parts of 2,4,5-trimethylfuran- 3-carboxylic chloride are added to the mixture. After the mixture has been stirred for 2 hours the dichloromethane phase is separated, dried over anhydrous sodium sulfate and evaporated. There is obtained 75 parts of N-cyclohexyl-2,4,5-trimethylfuran-3-hydroxamic acid in the form of an oil. This oil is dissolved in 300 parts of dichloromethane. To this solution there is added 36 parts of sodium hydroxide in 200 parts of water and 75.6 parts of dimethyl sulfate and the whole is stirred for 2 hours. The dichloromethane phase is then separated, washed with water until neutral, dried over anhydrous sodium sulfate and evaporated. Upon distillation of the residue there is obtained 52 parts of O-methyl-N-cyclohexyl-2,4,5-trimethylfuran-3-hydroxamic acid having a boiling point at 0.3 mm Hg of 128° to 130° C and the refractive index nD25 : 1.5021. ##SPC11##

Workup

  1. customis separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-69d4ab0d52e04d5394e67c84a103ebd5
Source dataset
uspto-grants-1976_11
Patent number
US03993772

Linked notes

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