4-Methoxybenzoic Acid → HCID 12851812, compound

HRID 1031909Notes

Reaction equation

HRID 1031909 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C([N:19]1[CH:23]=[CH:22]N=C1)(N1C=CN=C1)=O.[CH3:24][C:25]1[CH:26]=[C:27](CCN)[CH:28]=[CH:29][CH:30]=1>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:19][CH2:23][CH2:22][C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:24])=[O:9])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 74784-Methoxybenzoic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 4100852-(3-Methylphenyl)ethan-1-amine

Product 1

HCID 12851812HCID 12851812, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-methoxybenzoic acid (5.7 g, 0,038 mol) and carbonyldiimidazole (6.1 g, 0.050 mol) in 100 ml of THF was stirred for 1 h protected from moisture. To this was added 2-(3-methylphenyl) ethylamine and stirring was continued overnight. The reaction mixture was diluted with water (500 ml) and extracted with two 150 ml portions of methylene chloride. The methylene chloride solution was washed with 250 ml of water and evaporated to give the crystalline amide which was recrystallized from CH3OH/water to give 6.8 g (67%) H1, mp 87-92°.

Workup

  1. extractionextracted with two 150 ml portions of methylene chloride
  2. washThe methylene chloride solution was washed with 250 ml of water
  3. customevaporated

Sources & evidence

ORD record
ord-0148a68e64a1482f9f235f3cd108aab3
Source dataset
uspto-grants-1990_09
Patent number
US04956371

Reaction notes

Loading…