Diethyl Ether → HCID 19917987, compound

HRID 1755874Notes

Reaction equation

HRID 1755874 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:11][OH:12])=[O:10])=[CH:5][CH:4]=1.[OH:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].C(N(C(C)C)C(C)C)C.C(OCC)C>CN(C)C=O.[I-].[K+]>[OH:12][NH:11][C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][O:13][N:14]2[C:15](=[O:24])[C:16]3=[CH:23][CH:22]=[CH:21][CH:20]=[C:17]3[C:18]2=[O:19])=[CH:4][CH:5]=1)=[O:10]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10665N-HydroxyphthalimideHCID 81531DiisopropylethylamineHCID 158531224-(Chloromethyl)-N-hydroxybenzamide

Product 1

HCID 19917987HCID 19917987, compound

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

α-Chloro-N-hydroxy-p-toluamide, 6.52 g (40 mmol) of N-hydroxyphthalimide (7.4 g) (40 mmol) and 0.28 g of potassium iodide are dissolved in 50 ml of absolute dimethylformamide and treated with 5.16 g (40 mmol) of N-ethyldiisopropylamine while stirring. After stirring at room temperature for 16 hours 50 ml of diethyl ether are added. The precipitated product is filtered off under suction and washed with diethyl ether. There are obtained 7.5 g of N-hydroxy-α-(phthalimidooxy)-p-toluamide as a white powder of m.p. 202° C. (dec.).

Workup

  1. additionare added
  2. filtrationThe precipitated product is filtered off under suction
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-7ade8a000bfb4554a2d33003fd9eb012
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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