Ethyl chloroformate → HCID 14772178, compound

HRID 477469Notes

Reaction equation

HRID 477469 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[N:10]=1)[CH3:2].[H-].[Na+].[H][H].[CH2:26]([O:28][C:29](Cl)=[O:30])[CH3:27]>O1CCCC1.C(OCC)C>[C:29]([N:13]1[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:1][CH3:2])=[N:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[N:12]1)([O:28][CH2:26][CH3:27])=[O:30]

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 1220003-(2-Ethylphenyl)-5-(3-methoxyphenyl)-1H-1,2,4-triazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 14772178HCID 14772178, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.58 g (0.02 mole) of 5-(2-ethylphenyl)-3-(3-methoxyphenyl)-1H-1,2,4-triazole in 50 ml of anhydrous tetrahydrofuran, 0.66 g (0.02 mole) of an 80% oily suspension of sodium hydride were added. After the hydrogen development had ceased, a solution of 2 ml. (0.02 mole) of ethylchlorocarbonate in 20 ml of anhydrous tetrahydrofuran was added dropwise under stirring and the temperature was kept at 15°-20° C. Stirring was continued for 2,5 hours then, after adding 200 ml of anhydrous diethyl ether, the reaction mixture was filtered under vacuum and the filtrate brought to pH 3 by means of hydrogen chloride. The little amount of unreacted starting triazole which precipitated as the hydrochloride was filtered under vacuum, the filtrate was added with solid sodium bicarbonate and the resulting mixture stirred five minutes. After filtering the inorganic salts, the solution was concentrated to about 30 ml and kept overnight at about -10° C. 3.65 Grams of the compound of the title were obtained. M.p. 80°-82° C. Δ δ=-0.30.

Workup

  1. customwas kept at 15°-20° C
  2. stirringStirring
  3. waitwas continued for 2,5 hours
  4. filtrationthe reaction mixture was filtered under vacuum
  5. customprecipitated as the hydrochloride
  6. filtrationwas filtered under vacuum
  7. additionthe filtrate was added with solid sodium bicarbonate
  8. stirringthe resulting mixture stirred five minutes
  9. filtrationAfter filtering the inorganic salts
  10. concentrationthe solution was concentrated to about 30 ml
  11. custom3.65 Grams of the compound of the title were obtained

Sources & evidence

ORD record
ord-72435f11a87048fc83e705fa5a2146c0
Source dataset
uspto-grants-1989_12
Patent number
US04888350

Reaction notes

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