Benzaldehyde → HCID 66643754, compound

HRID 1695439Notes

Reaction equation

HRID 1695439 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[O-]CC.[Na+].Cl>C(O)C>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:7]2[C:6]([C:4]([OH:3])=[O:5])=[C:10](/[CH:11]=[CH:19]/[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:9][N:8]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 66643827Ethyl 3-(4-chlorophenyl)-5-methylisoxazole-4-carboxylate

Product 1

HCID 66643754HCID 66643754, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3-(4-chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (9.6 g, 36.1 mmol) and benzaldehyde (3.69 mL, 36.1 mmol) in ethanol (54 mL) was added sodium ethoxide (2.71 M, 14.6 mL, 39.7 mmol) and the reaction was heated under reflux for 10 min. Hydrochloric acid (1 N, 43.4 mL) was added and the resulting mixture was then triturated with dichloromethane and filtered to afford the title compound (6.21 g, 53%) as a light yellow solid. MS: m/e=324.1 [M−H]−.

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 10 min
  3. customthe resulting mixture was then triturated with dichloromethane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-5f108594194e4bbb8d39b372b349a111
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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