Sulfuric Acid → 103353-87-3

HRID 1588011Notes

Reaction equation

HRID 1588011 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 90 L 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 20 L of methylene chloride. The aqueous phase is mixed with 40 L of methylene chloride and basified with 19 L 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 20 L of methylene chloride
  3. additionThe aqueous phase is mixed with 40 L of methylene chloride and basified with 19 L 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-035d746daed94d85b518dbe2a241ef59
Source dataset
uspto-grants-1993_06
Patent number
US05220019

Reaction notes

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