Water → HCID 19981142, compound

HRID 1460906Notes

Reaction equation

HRID 1460906 reaction equation
[Cl:1][C:2]1[C:20]([CH3:21])=[CH:19][CH:18]=[C:4]2[C:5]([N:7]([C:10]3([C:16]#[N:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[C:8](=[O:9])[C:3]=12)=[O:6].S(=O)(=O)(O)[OH:23].O>C(Cl)Cl>[Cl:1][C:2]1[C:20]([CH3:21])=[CH:19][CH:18]=[C:4]2[C:5]([N:7]([C:10]3([C:16]([NH2:17])=[O:23])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[C:8](=[O:9])[C:3]=12)=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 19981144HCID 19981144, compound

Product 1

HCID 19981142HCID 19981142, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of about 4.35 g (14.4 mmol) of 3-chloro-N-(1-cyanocyclohexyl)-4-methylphthalimide in about 50 ml methylene chloride is added to concentrated sulfuric acid and water at less than 10° C. with rapid stirring. The reaction mixture is stirred very vigorously at ambient temperatures for 4 hours (reaction complete by thin layer chromatography), poured over crushed ice and extracted with about 450 ml methylene chloride. The organic extracts are combined and concentrated in vacuo to give a white fluffy precipitate. The precipitate is filtered and air dried to give the title product, 2.86 g (62% yield), mp 192° C.-208° C., identified by infrared and NMR analysis.

Workup

  1. custom(reaction complete by thin layer chromatography)
  2. additionpoured
  3. customover crushed ice
  4. extractionextracted with about 450 ml methylene chloride
  5. concentrationconcentrated in vacuo
  6. customto give a white fluffy precipitate
  7. filtrationThe precipitate is filtered
  8. customair dried

Sources & evidence

ORD record
ord-0a4f478a77e344a98a9adc4a8b6034de
Source dataset
uspto-grants-1991_12
Patent number
US05073190

Reaction notes

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