Propylamine → HCID 12788053, compound

HRID 1577805Notes

Reaction equation

HRID 1577805 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=O.O1CCCC1.[CH2:17]([NH2:20])[CH2:18][CH3:19]>O>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([NH:20][CH2:17][CH2:18][CH3:19])=[O:3])=[CH:5][CH:6]=1)=[O:9]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 8028TetrahydrofuranHCID 120884-Formylbenzoic acid

Product 1

HCID 12788053HCID 12788053, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15.0 g. of 4-carboxybenzaldehyde, 17.0 g. of N,N'-carbonyldiimidazole and 100 ml. of tetrahydrofuran is allowed to stand at room temperature for 3 hours, then 9.8 ml. of N-propylamine are added. The reaction mixture is allowed to stand at room temperature for 18 hours and is then heated at reflux temperature for one hour, diluted with water and concentrated. The oil which separates is washed twice with water and then purified by partition chromatography to yield p-formyl-N-propylbenzamide, m.p. 71°-74° C.

Workup

  1. additionA mixture of 15.0 g
  2. waitto stand at room temperature for 18 hours
  3. temperatureis then heated
  4. temperatureat reflux temperature for one hour
  5. concentrationconcentrated
  6. washThe oil which separates is washed twice with water
  7. custompurified
  8. customby partition chromatography

Sources & evidence

ORD record
ord-bdea35a9544f4401bf4e10fca304c068
Source dataset
uspto-grants-1981_09
Patent number
US04289769

Reaction notes

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