Ethyl isocyanate → HCID 18979206, compound

HRID 2393194Notes

Reaction equation

HRID 2393194 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:18]2[C:19](=[O:30])[C:20]3[C:25]([C:26](=[O:29])[C:27]=2[CH3:28])=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][OH:17])=[O:15])=[CH:5][CH:4]=1.[CH2:31]([N:33]=[C:34]=[O:35])[CH3:32]>C1COCC1>[CH2:31]([NH:33][C:34]([O:17][NH:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:18]1[C:19](=[O:30])[C:20]2[C:25]([C:26](=[O:29])[C:27]=1[CH3:28])=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:35])[CH3:32]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 9822660HCID 9822660, compound

Product 1

HCID 18979206HCID 18979206, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-(4-methoxyphenyl)-6-(3-methyl-1,4-naphthoquinon-2-yl)hexanohydroxamic acid (0.5 g) in THF was added a THF (2 ml) solution of ethyl isocyanate (0.1 g) at room temperature and the mixture was stirred for 2 hours. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1). The resulting oil was crystallized from hexane to provide the title compound (0.29 g).

Workup

  1. distillationThe solvent was then distilled off under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1)
  3. customThe resulting oil was crystallized from hexane

Sources & evidence

ORD record
ord-dd7b14b76ecd4ff6ac257368f67808ab
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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