Pyridine → 4-[N-4-chlorophenyl-N-methyl(Carbamoylmethyl)]-2-propionamidothiazole

HRID 224496Notes

Reaction equation

HRID 224496 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8](=[O:18])[N:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH3:10])[N:6]=1.N1C=CC=CC=1.[C:25](Cl)(=[O:28])[CH2:26][CH3:27]>COCCOC>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([N:9]([CH3:10])[C:8]([CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:25](=[O:28])[CH2:26][CH3:27])[S:3][CH:4]=2)=[O:18])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 544847172-amino-4-[N-4-chlorophenyl-N-methyl(carbamoylmethyl)] thiazole

Product 1

HCID 233333824-[N-4-chlorophenyl-N-methyl(Carbamoylmethyl)]-2-propionamidothiazoleYield 52.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A 300 ml reaction flask was charged with 6.0 g (0.021 mole) of 2-amino-4-[N-4-chlorophenyl-N-methyl(carbamoylmethyl)] thiazole, 100 ml of 1,2-dimethoxyethane and 2.6 g (0.03 mole) of pyridine. The propionyl chloride (2.8 g, 0.03 mole) which was dissolved in 15 ml of 1,2-dimethoxyethane was added portionwise and the reaction solution was heated at 65° for two hours. The solvent was evaporated and the residue was dissolved in ethyl acetate. The organic phase was extracted with water and dried over sodium sulfate. After evaporating most of the ethyl acetate, hexane was added. There was obtained 3.7 g (51%) of product, M.P. 153°-5°. N.M.R. (CDCl3) ∂1.2-1.4 (CH3), 2.3-2.5 (CH2), 3.3 (NCH3), 3.5 (0=CCH2), 6.5 (hetero-aromatic) 7.2-7.4 (aromatic).

Workup

  1. customA 300 ml reaction flask
  2. additionwas added portionwise
  3. temperaturethe reaction solution was heated at 65° for two hours
  4. customThe solvent was evaporated
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. extractionThe organic phase was extracted with water
  7. dry with materialdried over sodium sulfate
  8. customAfter evaporating most of the ethyl acetate, hexane
  9. additionwas added

Sources & evidence

ORD record
ord-98b053b6aa9f4f2ca4efd934fc533810
Source dataset
uspto-grants-1980_11
Patent number
US04232163

Reaction notes

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