p-Toluenesulfonic acid → HCID 21496692, compound

HRID 1730248Notes

Reaction equation

HRID 1730248 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)(=O)[CH3:2].[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([F:21])[CH:15]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([N:18]2[C:1](=[CH2:2])[C:4]3[C:5](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:6]2=[O:8])=[C:16]([F:21])[CH:15]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 684742-Acetylbenzoic acidHCID 938984-Chloro-2-fluoroaniline

Product 1

HCID 21496692HCID 21496692, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 8.2 parts of 2-acetylbenzoic acid, 7.27 parts of 4-chloro-2-fluoroaniline and 0.01 part of p-toluene-sulfonic acid was heated in an oil bath with occasional stirring at 150°-170° for 2 hours. The melt was poured into 100 parts of chloroform and washed successively with 50 parts of 10% aqueous hydrochloric acid solution, 50 parts of 10% aqueous sodium carbonate solution and 100 parts of a saturated aqueous sodium chloride solution. After drying the organic phase with anhydrous sodium sulfate, the solvent was evaporated at 300 mm. Hg at 50° C and the residue was crystallized from 100 parts of methanol to yield 8 parts of 2-(4-chloro-2-fluorophenyl)-3-methylene-1H-isoindol-1-one melting 86°-87°.

Workup

  1. temperaturewas heated in an oil bath
  2. washwashed successively with 50 parts of 10% aqueous hydrochloric acid solution, 50 parts of 10% aqueous sodium carbonate solution and 100 parts of a saturated aqueous sodium chloride solution
  3. dry with materialAfter drying the organic phase with anhydrous sodium sulfate
  4. customthe solvent was evaporated at 300 mm. Hg at 50° C
  5. customthe residue was crystallized from 100 parts of methanol

Sources & evidence

ORD record
ord-29476c6527294e99b5cde938ee475af1
Source dataset
uspto-grants-1976_11
Patent number
US03992189

Reaction notes

Loading…