Hydrochloric Acid → HCID 4872096, compound

HRID 1055205Notes

Reaction equation

HRID 1055205 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].[C:10](OCC)(=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl>C(OCC)C>[CH3:3][N:4]1[CH2:8][CH2:7][CH:6]([C:10](=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]1=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydride

Product 1

HCID 4872096HCID 4872096, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

13.20 g of 60% NaH (in paraffin oil) (0.33 mol) was added to 100 ml of dry diethyl ether. With vigorous stirring, 19.83 g (0.20 mol) of N-methylpyrrolidone were added. Then within one hour 121.30 g (0.83 mol) of diethyl oxalate were added dropwise. After the addition the suspension was heated to 40° C. and stirred for 21 hours. The reaction mixture was then cooled in an ice bath, mixed with 66 ml 5M HCl and the resulting 2-phase mixture was filtered once. Then the two phases were separated, and the aqueous phase was extracted twice with 100 ml diethyl ether. The combined ethereal phases were dried over Na2SO4 and concentrated on a rotary evaporator to dryness. The oily residue was cooled to −80° C. and mixed with 200 ml diethyl ether. The resulting brown solid was filtered off and recrystallized from heptane. This gave 5.2 g product as white needles.

Workup

  1. additionAfter the addition the suspension
  2. temperatureThe reaction mixture was then cooled in an ice bath
  3. filtrationthe resulting 2-phase mixture was filtered once
  4. customThen the two phases were separated
  5. extractionthe aqueous phase was extracted twice with 100 ml diethyl ether
  6. dry with materialThe combined ethereal phases were dried over Na2SO4
  7. concentrationconcentrated on a rotary evaporator to dryness
  8. temperatureThe oily residue was cooled to −80° C.
  9. additionmixed with 200 ml diethyl ether
  10. filtrationThe resulting brown solid was filtered off
  11. customrecrystallized from heptane

Sources & evidence

ORD record
ord-7fd9735e1dee453e8bc3ce9e99bb5328
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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