Sulfuric Acid → 1-(3-chlorophthalimido)cyclohexanecarboxamide

HRID 328297Notes

Reaction equation

HRID 328297 reaction equation
[Cl:1][C:2]1[CH:20]=[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:22]>C(Cl)Cl>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:4]2[C:5]([N:7]([C:10]3([C:16]([NH2:17])=[O:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[C:8](=[O:9])[C:3]=12)=[O:6]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 21441241HCID 21441241, compound

Product 1

HCID 932671-(3-chlorophthalimido)cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 300 mgs. 3-chloro-N-(1-cyanocyclohexyl)-phthalimide in 3 ml. methylene chloride is added, with good stirring, 0.38 ml. concentrated sulfuric acid. After 0.5 hour, ice is added and the aqueous phase extracted with chloroform. The organic phase is washed with water, dried and evaporated to give the 1-(3-chlorophthalimido)cyclohexanecarboxamide which can be purified by recrystallization from aqueous ethanol, m.p. 193°-194° C.

Workup

  1. additionTo a solution containing 300 mgs
  2. additionice is added
  3. extractionthe aqueous phase extracted with chloroform
  4. washThe organic phase is washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-6f55ce4af80c4f59a71482c35b93e93c
Source dataset
uspto-grants-1977_04
Patent number
US04017299

Reaction notes

Loading…