Diethylhydroxylamine → HCID 20337386, compound

HRID 1706147Notes

Reaction equation

HRID 1706147 reaction equation
[CH3:1][C:2]([O:4][C:5]1[C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH2:14]([N:16]([CH2:18][CH3:19])[OH:17])[CH3:15]>CCOCC>[C:2]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:11]([O:17][N:16]([CH2:18][CH3:19])[CH2:14][CH3:15])=[O:12])(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 19463DiethylhydroxylamineHCID 796682-Acetoxybenzoyl chloride

Product 1

HCID 20337386HCID 20337386, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To 9.1 g (0.0455 mol) of aspirin chloride dissolved in 100 ml of ether was added 8.1 g (0.09 mol) of N,N-diethylhydroxylamine dissolved in 100 ml of ether. The resulting suspension was filtered and the filtrate was diluted with 800 ml of heptane and filtered again. The ether-heptane filtrate was then concentrated in vacuo to give the desired compound (E) as a light yellow oil in 84% yield: TLC (silica gel, ehter) Rf =0.39; IR (neat) broad band 1760-1730 cm-1 (s) (C=O); NMR (CDCl1)δ8.1.7.0 (m, 4, aromatic-H), 3.0 (q, 4, J=7 Hz, CH3CH2 --N), 2.33 (s, 3, CH3C--O2) and 1.18 (t, 6, J=7 Hz, CH3CH2 --N).

Workup

  1. filtrationThe resulting suspension was filtered
  2. additionthe filtrate was diluted with 800 ml of heptane
  3. filtrationfiltered again
  4. concentrationThe ether-heptane filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-859eaedb8c4a4b2192c5e3bfb73cc5c1
Source dataset
uspto-grants-1980_06
Patent number
US04206220

Reaction notes

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