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

HRID 1689800
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HRID 1689800 반응식
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]
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 8857
Ethyl Acetate
용매

실험 절차

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 as a (1275.36 g, 64% yield) as a white solid. MS (m/e): 312 (M+1).

후처리

  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

출처 및 근거

ORD 기록
ord-50e235f7deac4f3c8093dacbb4d61c18
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08153624B2

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