Water → N-cyclopentyl-2,5-dimethylfuran-3-hydroxamic acid

HRID 1730808

Reaction equation

HRID 1730808 reaction equation
Cl.[CH:2]1([NH:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])O.[Na+].O.[CH3:15][C:16]1[O:17][C:18]([CH3:24])=[CH:19][C:20]=1[C:21](Cl)=[O:22]>ClCCl>[CH:2]1([N:7]([C:21]([C:20]2[CH:19]=[C:18]([CH3:24])[O:17][C:16]=2[CH3:15])=[O:22])[OH:8])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27348042,5-Dimethyl-3-furoyl ChlorideHCID 21496528N-cyclopentylhydroxylamine hydrochloride

Product 1

HCID 21496542N-cyclopentyl-2,5-dimethylfuran-3-hydroxamic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

27.5 Parts of N-cyclopentylhydroxylamine hydrochloride is dissolved in 200 parts of dichloromethane; a solution of 33.6 parts of sodium hydrogen carbonate in 300 parts of water is then added. At room temperature and while stirring thoroughly, 31.8 parts of 2,5-dimethylfuran-3-carboxylic chloride is dripped into this mixture. After stirring the mixture for 1 hour the organic phase is separated, dried over anhydrous sodium sulfate and evaporated. The oil which remains soon solidifies and the crystals obtained are stirred with petroleum ether, suction filtered and dried. There is obtained 14.3 parts of N-cyclopentyl-2,5-dimethylfuran-3-hydroxamic acid having a melting point of from 107° to 109° C. ##SPC9##

Workup

  1. stirringAfter stirring the mixture for 1 hour the organic phase
  2. customis separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customthe crystals obtained
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-560fb24bd6e944b08c3dccc8283e414f
Source dataset
uspto-grants-1976_11
Patent number
US03993772

Linked notes

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