Butanedioic acid, 2-acetyl-, 1,4-diethyl ester → HCID 178470721, compound

HRID 890167Notes

Reaction equation

HRID 890167 reaction equation
[C:1]([CH:4]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]([O:7]CC)=O)(=O)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:28]1([CH3:43])[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[C:29]=1[C:36]1[C:37]([CH3:42])=[N:38][NH:39][C:40]=1[NH2:41]>C1(C)C(C)=CC=CC=1>[C:28]1([CH3:43])[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[C:29]=1[C:36]1[C:37]([CH3:42])=[N:38][N:39]2[C:5](=[O:7])[C:4]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:1]([CH3:2])[NH:41][C:40]=12

Participants

5

Reactant 3

HCID 66197Butanedioic acid, 2-acetyl-, 1,4-diethyl esterHCID 521998p-Toluenesulfonic acid monohydrateHCID 178424562HCID 178424562, compound

Product 1

HCID 178470721HCID 178470721, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Diethyl acetylsuccinate (0.3 mL) and a catalytic amount of 4-toluenesulfonic acid monohydrate were added to a solution of 4-mesityl-3-methyl-1H-5-pyrazoleamine (100 mg) of Reference Example 1 in xylene (5 mL). Under heating under reflux, the mixture was stirred for three hours while distilling water off with Dean-Stark. The reaction solution was cooled, water was added thereto. the mixture was extracted twice with ethyl acetate, and washed twice with an aqeous saturated solution of sodium bicarbonate. The organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography, to give the title compound (200 mg) as a yellow amorphous material.

Workup

  1. temperatureUnder heating
  2. temperatureunder reflux
  3. distillationwhile distilling water off with Dean-Stark
  4. temperatureThe reaction solution was cooled
  5. additionwater was added
  6. extractionthe mixture was extracted twice with ethyl acetate
  7. washwashed twice with an aqeous saturated solution of sodium bicarbonate
  8. customThe organic layer was separated
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-36d3718327b04e97aa2dd146392959bb
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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