Water → HCID 15068914, compound

HRID 1031908Notes

Reaction equation

HRID 1031908 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:24][C:25]1[CH:26]=[C:27]([CH2:31][CH2:32][NH2:33])[CH:28]=[CH:29][CH:30]=1.O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:33][CH2:32][CH2:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([CH3:24])[CH:26]=1)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 114613-Methoxybenzoic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 4100852-(3-Methylphenyl)ethan-1-amine

Product 1

HCID 15068914HCID 15068914, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-methoxybenzoic acid (5.2 g, 0.034 mol) and carbonyldiimidazole (5.5 g, 0.034 mol) in THF (200 ml) was stirred in a flask protected from moisture. To this solution was added 4.6 g (0.034 mol) of 2-(3-methylphenyl)ethylamine in a small volume of THF. Stirring was continued for 1 h and then the reaction mixture was poured into 500 ml of water and extracted twice with 100 ml portions of methylene chloride. The methylene chloride solution was washed with 5% HCl, 10% Na2CO3, and water. Evaporation of this solution afforded the amide G1 (8.7 g, 94%) as a viscous oil.

Workup

  1. extractionextracted twice with 100 ml portions of methylene chloride
  2. washThe methylene chloride solution was washed with 5% HCl, 10% Na2CO3, and water
  3. customEvaporation of this solution

Sources & evidence

ORD record
ord-087efde9446744b3a58d1edf1c356131
Source dataset
uspto-grants-1990_09
Patent number
US04956371

Reaction notes

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