2-Benzoylbenzoic Acid → HCID 21398385, compound

HRID 1439172Notes

Reaction equation

HRID 1439172 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][NH:19][CH2:20][CH2:21][NH2:22]>ClC1C=CC=CC=1>[CH3:18][N:19]1[C:1]2([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:9]3[C:10]([C:11](=[O:13])[N:22]2[CH2:21][CH2:20]1)=[CH:14][CH:15]=[CH:16][CH:17]=3

Participants

4

Reactant 2

HCID 68132-Benzoylbenzoic AcidHCID 8014N-Methylethylenediamine

Product 1

HCID 21398385HCID 21398385, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

22.6 Parts of o-benzoyl-benzoic acid are dissolved in 100 ml of chlorobenzene. 7.4 Parts of N-methylethylenediamine are added within 10 minutes. The temperature is then raised within 1 - 2 hours to such an extent that some chlorobenzene is continuously distilled off with the reaction water until the boiling point of the pure chlorobenzene (130°-132°) is attained. 80-90% of the theoretical amount of reaction water can be removed from the distillate. The remainder of the chlorobenzene is distilled off from the reaction mass in vacuo and the viscous oil which remains is crystallised by the addition of about 10 parts of ethyl acetate. The 1-methyl-9b-phenyl-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one so obtained of the formula ##STR10## is filtered off and recrystallised from a mixture of 30 parts of ethyl acetate and 30 parts of petroleum ether (B.P. 30°-60° ). M.P. 120°-122°.

Workup

  1. distillationis continuously distilled off with the reaction water until the boiling point of the pure chlorobenzene (130°-132°)
  2. custom80-90% of the theoretical amount of reaction water
  3. customcan be removed from the distillate
  4. distillationThe remainder of the chlorobenzene is distilled off from the reaction mass in vacuo
  5. customthe viscous oil which remains is crystallised by the addition of about 10 parts of ethyl acetate

Sources & evidence

ORD record
ord-24274f9a5a2c41fdb1d96205cc632bc6
Source dataset
uspto-grants-1977_11
Patent number
US04058529

Reaction notes

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