Ethylamine → HCID 3049302, compound

HRID 1112726Notes

Reaction equation

HRID 1112726 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.[CH2:15]([NH2:17])[CH3:16]>C(O)C>[CH2:15]([NH:17][CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:6][N:7]=1)[CH3:16]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 7369662-(Chloromethyl)-5-(4-chlorophenyl)-1,3-oxazole

Product 1

HCID 3049302HCID 3049302, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.3 g of 2-chloromethyl-5-(4-chlorophenyl) oxazole in 50 ml of ethanol was added 3.2 g of 70% ethylamine aqueous solution, and the resultant solution was allowed to stand at room temperature overnight. At the end of this time, the solvent and the excess ethylamine were distilled off under reduced pressure, and then 30 ml of water, 10 ml of 2N NaOH solution and 50 ml of chloroform were added. The chloroform layer was separated and the aqueous layer was extracted twice with 30 ml of chloroform. The combined chloroform layer was dried over anhydrous sodium sulfate, and the solvent was removed in vacuo to give 2.1 g of crude 2-ethylaminomethyl-5-(4-chlorophenyl) oxazole. This was dissolved in 15 ml of ethanol, and 5 ml of ethanolic saturated hydrogen chloride solution was added. Evaporation of the solvent followed by recrystallization from ethanol afforded 2.0 g (73 percent) of 2-ethylaminomethyl-5-(4-chlorophenyl) oxazole hydrochloride, M. P. 194°-6° C.

Workup

  1. distillationAt the end of this time, the solvent and the excess ethylamine were distilled off under reduced pressure
  2. addition30 ml of water, 10 ml of 2N NaOH solution and 50 ml of chloroform were added
  3. customThe chloroform layer was separated
  4. extractionthe aqueous layer was extracted twice with 30 ml of chloroform
  5. dry with materialThe combined chloroform layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-57f9286ecf31489dbabdce958b8504c5
Source dataset
uspto-grants-1978_10
Patent number
US04123541

Reaction notes

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