Benzoic Acid → HCID 13121258, compound

HRID 1701991Notes

Reaction equation

HRID 1701991 reaction equation
[C:1]1([NH:7][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](O)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C1(C)C(C)=CC=CC=1>[C:12]1([CH:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10][NH:11][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 962WaterHCID 13121257HCID 13121257, compound

Product 1

HCID 13121258HCID 13121258, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of N,1-diphenyl-1,3-propanediamine (5.0 g, 22 mmoles, described in Example 2) and benzoic acid (12.5 g, 105 mmoles) in dry xylene (300 ml) is refluxed for 20 hr using a Dean-Stark water separator. The mixture is cooled and washed with several portions of 2 N hydrochloric acid. The aqueous extracts are combined, basified with dilute sodium hydroxide and extracted with chloroform. The organic extract is washed with brine, dried over magnesium sulfate and evaporated. The residue is chromatographed an silica gel using chloroform and the eluates are evaporated. The residue is crystallized from benzene-hexane to obtain the title compound (2.0 g), mp 120°-121° C.

Workup

  1. temperatureThe mixture is cooled
  2. washwashed with several portions of 2 N hydrochloric acid
  3. extractionextracted with chloroform
  4. extractionThe organic extract
  5. washis washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue is chromatographed an silica gel
  9. customthe eluates are evaporated
  10. customThe residue is crystallized from benzene-hexane

Sources & evidence

ORD record
ord-e141855f8de44ea69d4bbb74fcf48f8f
Source dataset
uspto-grants-1983_04
Patent number
US04379926

Reaction notes

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