p-Toluidine → 2-(3-chlorophenoxy)N-(4-methylphenyl)nicotinamide

HRID 1679799Notes

Reaction equation

HRID 1679799 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[N:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].[CH3:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[N:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH:23][C:22]1[CH:24]=[CH:25][C:19]([CH3:18])=[CH:20][CH:21]=1)=[O:9]

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 8471TriethylamineHCID 226121122-(3-Chlorophenoxy)nicotinoyl chloride

Product 1

HCID 128944272-(3-chlorophenoxy)N-(4-methylphenyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In the same manner as in Example 1(b), 1.1 grams (0.01 mole) 2(3-chlorophenoxy) nicotinoyl chloride, 1.0 grams (0.01 mole) 4-methylaniline, 1.0 grams (0.01 mole) triethylamine and 125 milliliters toluene were combined to yield 2.4 grams (70.9% of theoretical yield) of the desired product, m.p. 140°-143° C. The structure was confirmed by mass spectrometry.

Workup

  1. customto yield

Sources & evidence

ORD record
ord-4435580ea0974395af6c5108ee2c69a4
Source dataset
uspto-grants-1981_06
Patent number
US04270946

Reaction notes

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