Sulfuric Acid → 103353-87-3

HRID 1030303Notes

Reaction equation

HRID 1030303 reaction equation
[ClH:1].[C:2]([C:4]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=1)([CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[C:5]([CH:8](C(OCC)=O)[C:9]([O:11]CC)=O)([CH3:7])[CH3:6])#[N:3].S(=O)(=O)(O)[OH:34]>O>[ClH:1].[CH3:23][N:22]([CH3:24])[CH2:21][CH2:20][CH2:19][C:4]1([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=2)[C:5]([CH3:7])([CH3:6])[CH2:8][C:9](=[O:11])[NH:3][C:2]1=[O:34]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 17973432HCID 17973432, compound

Product 1

HCID 9951187103353-87-3

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A reaction vessel is charged with 11.24 kg of diethyl 2-[2-cyano-5-(dimethylamino)-2-(3-methoxyphenyl)-1,1-dimethylpentyl]propanedioate, monohydrochloride (9), and a solution of 11.46 kg of sulfuric acid (96% w/w) in 90L of water is added. The reaction mixture is refluxed for about 54 h. When the reaction is complete as indicated by thin layer chromatography, the solution is cooled to 25° C. The aqueous solution is washed with 20L of methylene chloride. The aqueous phase is mixed with 40L of methylene chloride and basified with 19L of aqueous ammonium hydroxide (29% w/w) while maintaining the temperature at less than 30° C. After separation of the layers, the aqueous phase is extracted twice with 20-L portions of methylene chloride. The combined organic phase is washed twice with 20-L portions of water and filtered through a layer of diatomaceous earth.

Workup

  1. temperatureThe reaction mixture is refluxed for about 54 h
  2. washThe aqueous solution is washed with 20L of methylene chloride
  3. additionThe aqueous phase is mixed with 40L of methylene chloride and basified with 19L of aqueous ammonium hydroxide (29% w/w)
  4. temperaturewhile maintaining the temperature at less than 30° C
  5. customAfter separation of the layers
  6. extractionthe aqueous phase is extracted twice with 20-L portions of methylene chloride
  7. washThe combined organic phase is washed twice with 20-L portions of water
  8. filtrationfiltered through a layer of diatomaceous earth

Sources & evidence

ORD record
ord-89f221b9ca65457d81f30940149e5d7f
Source dataset
uspto-grants-1992_04
Patent number
US05104990

Reaction notes

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