Potassium Carbonate → N-(thiazol-4-yl)methyl-2-ethyl-6-methylaniline

HRID 27339

Reaction equation

HRID 27339 reaction equation
Cl[CH2:2][C:3]1[N:4]=[CH:5][S:6][CH:7]=1.[CH2:8]([C:10]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:11]=1[NH2:12])[CH3:9].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[S:6]1[CH:7]=[C:3]([CH2:2][NH:12][C:11]2[C:13]([CH3:17])=[CH:14][CH:15]=[CH:16][C:10]=2[CH2:8][CH3:9])[N:4]=[CH:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 324852-Ethyl-6-methylanilineHCID 27632904-(Chloromethyl)-1,3-thiazole

Product 1

HCID 20534534N-(thiazol-4-yl)methyl-2-ethyl-6-methylanilineYield 39.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In 200 ml dry dimethylformamide was added 10.2 g 4-chloromethylthiazole, 10.26 g 2-ethyl-6-methylaniline and 10.54 g of potassium carbonate. The mixture was stirred at 100° C. for 3 days and filtered. The filtrate was stripped, dissolved in methylene chloride, washed with water, dried and stripped again. The crude product was chromatographed with methylene chloride through a 200-g silica-gel column to give 7 g of product.

Workup

  1. filtrationfiltered
  2. dissolutiondissolved in methylene chloride
  3. washwashed with water
  4. customdried
  5. customThe crude product was chromatographed with methylene chloride through a 200-g silica-gel column

Sources & evidence

ORD record
ord-b9e27a171eb14d4e9634988a95ba4bfe
Source dataset
uspto-grants-1980_09
Patent number
US04221584

Linked notes

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