Triethylamine → Methyl 5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazole-4-carboxylate

HRID 1689819Notes

Reaction equation

HRID 1689819 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10](=[O:17])[CH2:11][C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13].ClO[N:20]=[CH:21][C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29]>CCO.CCOC(C)=O>[CH3:8][O:9][C:10]([C:11]1[C:21]([C:22]2[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:29])=[N:20][O:13][C:12]=1[CH:14]1[CH2:16][CH2:15]1)=[O:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl EsterHCID 866424822,6-Dichloro-benzaldehyde chloro-oxime

Product 1

HCID 53421832Methyl 5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazole-4-carboxylateYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (1.82 L, 12.84 mol) is added to 3-cyclopropyl-3-oxo-propionic acid methyl ester (913 g, 6.42 mol) and the mixture is stirred at room temperature for 30 minutes. Then, the mixture is cooled to about 10° C. and a suspension of 2,6-dichloro-benzaldehyde chloro-oxime (1440.9 g, 6.42 mol) in EtOH (3.2 L) is added slowly (the internal temperature does not exceed 24° C.). After the addition, the reaction is stirred overnight at room temperature. The reaction is diluted with EtOAc (5.3 L) and washed with water (1.7 L). The layers are separated and the aqueous layer is extracted with EtOAc (3 L). The combined organics are washed with brine, dried over Na2SO4 (anhyd), filtered and concentrated to about 10% of its total volume. The precipitate formed is filtered, triturated with ether (2 L) and dried under vacuum to obtain title compound (1275.36 g, 64% yield) as a white solid. MS (m/e): 312 (M+1).

Workup

  1. temperatureThen, the mixture is cooled to about 10° C.
  2. additionis added slowly (the internal temperature
  3. customdoes not exceed 24° C.
  4. additionAfter the addition
  5. stirringthe reaction is stirred overnight at room temperature
  6. washwashed with water (1.7 L)
  7. customThe layers are separated
  8. extractionthe aqueous layer is extracted with EtOAc (3 L)
  9. washThe combined organics are washed with brine
  10. dry with materialdried over Na2SO4 (anhyd)
  11. filtrationfiltered
  12. concentrationconcentrated to about 10% of its total volume
  13. customThe precipitate formed
  14. filtrationis filtered
  15. customtriturated with ether (2 L)
  16. customdried under vacuum

Sources & evidence

ORD record
ord-86627788598c4392949af9c85fdbec25
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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