Triethylamine → HCID 21496529, compound

HRID 1730813

Reaction equation

HRID 1730813 reaction equation
C(N(CC)CC)C.Cl.[CH:9]1([NH:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10]1.[CH3:16][C:17]1[O:18][CH:19]=[CH:20][C:21]=1[C:22](Cl)=[O:23]>C1C=CC=CC=1>[CH:9]1([N:14]([C:22]([C:21]2[CH:20]=[CH:19][O:18][C:17]=2[CH3:16])=[O:23])[OH:15])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27598502-Methylfuran-3-carbonyl chlorideHCID 21496528N-cyclopentylhydroxylamine hydrochloride

Product 1

HCID 21496529HCID 21496529, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

30 Parts of triethylamine is added to a suspension of 20 parts of N-cyclopentylhydroxylamine hydrochloride in 300 parts of benzene and the whole is stirred for 1 hour. At room temperature, 10 parts of 2-methylfuran-3-carboxylic chloride is dripped in. After the mixture has been stirred for a further 3 hours it is suction filtered, the residue is washed with benzene, and the organic phase is washed with water, dried with sodium sulfate and evaporated. There is obtained 25 parts of N-cyclopentyl-2-methylfuran-3-hydroxamic acid in the form of an oil. This oil is dissolved in 300 parts of dichloromethane; while stirring and at room temperature, 16 parts of sodium hydroxide in 70 parts of water, and 26 parts of dimethyl sulfate are added to the solution. After the mixture has been stirred for 2 hours the organic phase is separated, washed with water until neutral and dried with anhydrous sodium sulfate. Distillation gives 21 parts of O-methyl-N-cyclopentyl-2-methylfuran- 3-hydroxamic acid having a boiling point at 0.01 mm Hg of 104° to 108° C and the refractive index nD25 : 1.5073. ##SPC14##

Workup

  1. customAt room temperature
  2. stirringAfter the mixture has been stirred for a further 3 hours it
  3. filtrationfiltered
  4. washthe residue is washed with benzene
  5. washthe organic phase is washed with water
  6. dry with materialdried with sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-fde7138661a444c3a0850e0d1c477f10
Source dataset
uspto-grants-1976_11
Patent number
US03993772

Linked notes

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