Water → HCID 18945618, compound

HRID 399930Notes

Reaction equation

HRID 399930 reaction equation
C[O-].[Na+].[OH:4][N:5]1[C:9](=[O:10])[CH:8]2[CH2:11][CH2:12][CH:13]=[CH:14][CH:7]2[C:6]1=[O:15].[CH2:16](Cl)[CH3:17].O>CO>[CH2:16]([O:4][N:5]1[C:6](=[O:15])[CH:7]2[CH2:14][CH2:13][CH:12]=[CH:11][CH:8]2[C:9]1=[O:10])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6337Chloroethane2×HCID 10942334Sodium MethoxideHCID 21940951HCID 21940951, compound

Product 1

HCID 18945618HCID 18945618, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

In an autoclave a solution of 3.5 g of sodium methoxide (0.065 mol) in 40 ml of methanol, 11.0 g of N-hydroxytetra-hydrophthalimide (0.066 mol) and 4.6 g (0.072 mol) of ethyl chloride were mixed together. The mixture was heated to 100° C. After reaching this temperature the mixture was stirred for a further 5 hours while the temperature was held at 100° C. After 5 hours' reaction the excess ethyl chloride was blown out and the reaction mixture was discharged. The reaction mixture comprised a large quantity of solid material. This was dissolved by the addition of water and the whole was afterwards extracted with toluene to obtain the product. Gas chromatographic analysis of the toluene extract showed that the yield was 74% of N-ethoxytetra-hydrophthalimide (0.049 mol).

Workup

  1. customwas held at 100° C
  2. extractionthe whole was afterwards extracted with toluene
  3. customto obtain the product
  4. extractionGas chromatographic analysis of the toluene extract

Sources & evidence

ORD record
ord-93d40f7eaf5347b8960b2cb888e4a06c
Source dataset
uspto-grants-1998_10
Patent number
US05824804

Reaction notes

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