Tetrahydrofuran → HCID 13255895, compound

HRID 268210Notes

Reaction equation

HRID 268210 reaction equation
C([NH+](CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]([CH2:20][Cl:21])=[N:18][C:17]([C:22]([O-])=[O:23])=[N:16]2)=[C:11]([C:25](=[O:34])[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[CH:10]=1.O1CCCC1.C(Cl)(=O)OCC.[NH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]([CH2:20][Cl:21])=[N:18][C:17]([C:22]([N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)=[O:23])=[N:16]2)=[C:11]([C:25](=[O:34])[C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8083MorpholineHCID 10928Ethyl chloroformateHCID 131710107HCID 131710107, compound

Product 1

HCID 13255895HCID 13255895, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 5.07 parts of 1-[4-chloro-2-(4-methoxybenzoyl)phenyl]-5-chloromethyl-1H-1,2,4-triazole-3-carboxylic acid triethylammonium salt in 60 volume parts of dry tetrahydrofuran, 1.0 volume part of ethyl chlorocarbonate is added under cooling with ice-salt. After 5 minutes a solution of 2.6 volume parts of morpholine in 3 volume parts of dry tetrahydrofuran is added to the mixture. After stirring for an additional 5 minutes the reaction mixture is diluted with water and concentrated under reduced pressure. The concentrate is extracted with ethyl acetate and the ethyl acetate layer is washed with water. After evaporation of the solvent the residue is treated with ethanol-ether to yield 1-[4-chloro-2-(4-methoxybenzoyl)phenyl]-5-chloromethyl-3-morpholinocarbonyl-1H-1,2,4-triazole as crystals. Recrystallization from aqueous ethanol gives colorless prisms melting at 180°-181°C. The crystals are hemihydrate.

Workup

  1. additionis added
  2. concentrationconcentrated under reduced pressure
  3. extractionThe concentrate is extracted with ethyl acetate
  4. washthe ethyl acetate layer is washed with water
  5. customAfter evaporation of the solvent the residue
  6. additionis treated with ethanol-ether

Sources & evidence

ORD record
ord-4bbe3f2e9f924e7a9900106ffb1cde38
Source dataset
uspto-grants-1976_03
Patent number
US03947417

Reaction notes

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