Triethylamine → N-cyclohexyl-2-methylfuran-3-hydroxamic acid

HRID 1730806Notes

Reaction equation

HRID 1730806 reaction equation
Cl.[CH:2]1([NH:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:17][C:18]1[O:19][CH:20]=[CH:21][C:22]=1[C:23](Cl)=[O:24]>C1C=CC=CC=1>[CH:2]1([N:8]([C:23]([C:22]2[CH:21]=[CH:20][O:19][C:18]=2[CH3:17])=[O:24])[OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27598502-Methylfuran-3-carbonyl chlorideHCID 3084432N-Cyclohexylhydroxylamine hydrochloride

Product 1

HCID 21496539N-cyclohexyl-2-methylfuran-3-hydroxamic acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

57 parts (by weight) of N-cyclohexylhydroxylamine hydrochloride is added to 800 parts of benzene; 71 parts of triethylamine is then introduced into this mixture. After the mixture has been stirred for 1 hour, a solution of 50 parts of 2-methylfuran-3-carboxylic chloride in 100 parts of benzene is dripped in at room temperature. After the mixture has been stirred for 3 hours the precipitate is filtered and washed with benzene. The filtrate is washed with water, dried over sodium sulfate and evaporated. The crystalline residue is recrystallized from cyclohexane. There is obtained 33 parts of N-cyclohexyl-2-methylfuran-3-hydroxamic acid, m.p.: 108°-110° C.

Workup

  1. customis dripped in at room temperature
  2. stirringAfter the mixture has been stirred for 3 hours the precipitate
  3. filtrationis filtered
  4. washwashed with benzene
  5. washThe filtrate is washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe crystalline residue is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-ae5fa0bc08194526a1a49eb850188d14
Source dataset
uspto-grants-1976_11
Patent number
US03993772

Reaction notes

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