2-Benzoylbenzoic Acid → HCID 21398396, compound

HRID 1439173Notes

Reaction equation

HRID 1439173 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.[CH2:18]([NH:21][CH2:22][CH2:23][CH2:24][NH2:25])[CH2:19][CH3:20].ClC1C=CC=CC=1Cl>O>[CH2:18]([N:21]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:25]2[CH2:24][CH2:23][CH2:22]1)=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 68132-Benzoylbenzoic AcidHCID 72391,2-DichlorobenzeneHCID 90250N-Propylpropane-1,3-diamine

Product 1

HCID 21398396HCID 21398396, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

22.6 Parts of o-benzoyl-benzoic acid and 11.6 parts of N-propyl-1,3-propanediamine are haeted within 11/2 hours with 50 parts by volume of o-dichlorobenzene until the boiling point of the latter is attained. Almost the theoretical amount of reaction water is azeotropically distilled off. The clear solution is evaporated to dryness in vacuo, the oily residue is dissolved in ethyl acetate and crystallised by the dropwise addition of pentane. In this way, 1-propyl-10b-phenyl-1,3,4,10b-tetrahydro-pyrimido[2,1-a]isoindol-6(2H)-one is obtained of the formula ##STR19## M.P. 135°-137°. 1-Ethyl-10b-phenyl-1,3,4,10b-tetrahydro-pyrimido[2,1-a]isoindol -6(2H)-one is obtained in the same manner from o-benzoyl-benzoic acid and N-ethyl-1,3-propanediamine. M.P. 131°-133°.

Workup

  1. custom2 hours
  2. distillationis azeotropically distilled off
  3. customThe clear solution is evaporated to dryness in vacuo
  4. dissolutionthe oily residue is dissolved in ethyl acetate
  5. customcrystallised by the dropwise addition of pentane

Sources & evidence

ORD record
ord-9ec9e32eb84549c7a900d2c8f12a4ce5
Source dataset
uspto-grants-1977_11
Patent number
US04058529

Reaction notes

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