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Hydrochloric Acid → 2-methoxyacetamido-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide

HRID 648731
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HRID 648731 반응식
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH:11][C:12](=[O:14])[CH3:13].[CH3:15][O:16][CH2:17][C:18]1[O:23][C:22](=[O:24])[C:21]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([F:32])([F:31])[F:30])[C:20]=2[N:19]=1.Cl>O1CCCC1.CCCCCC>[CH3:15][O:16][CH2:17][C:18]([NH:19][C:20]1[C:28]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](=[O:24])[CH2:13][C:12]([NH:11][C:7]1[S:6][CH:10]=[CH:9][N:8]=1)=[O:14])=[O:23]
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 176252-AcetamidothiazoleHCID 133813284H-3,1-Benzoxazin-4-one, 2-(methoxymethyl)-8-(trifluoromethyl)-HCID 178418339Butyllithium

생성물 1

HCID 133813462-methoxyacetamido-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide수율 67.3%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
2회
HCID 8058Hexane용매

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온도
0 °C

실험 절차

150 ml of a solution of 1.5 moles of butyllithium per liter of hexane were added over 20 minutes at 0° C. to a solution of 15.73 g of N-(2-thiazolyl)-acetamide in 550 ml of tetrahydrofuran and the mixture was stirred at 0° C. for 10 minutes and was cooled to -70° C. A solution of 14.4 g of the product of Step A in 165 ml of tetrahydrofuran was added at -70° C. over 15 minutes to the mixture which was then stirred at -70° C. for 30 minutes and poured into a mixture of ice and N hydrochloric acid. The mixture was extracted with ether and the combined organic phases were washed successively with hydrochloric acid and water, dried and evaporated to dryness under reduced pressure at 20° to 30° C. The residue was empasted with 250 ml of ether and was vacuum filtered. The product was washed with ether and dried under reduced pressure at 20° C. to obtain 15 g of 2-methoxyacetamido-β-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide melting at 152° C.

후처리

  1. temperaturewas cooled to -70° C
  2. stirringwas then stirred at -70° C. for 30 minutes
  3. extractionThe mixture was extracted with ether
  4. washthe combined organic phases were washed successively with hydrochloric acid and water
  5. customdried
  6. customevaporated to dryness under reduced pressure at 20° to 30° C
  7. filtrationfiltered
  8. washThe product was washed with ether
  9. customdried under reduced pressure at 20° C.

출처 및 근거

ORD 기록
ord-b8ab7c00869c445887216c63284d421e
출처 데이터셋
uspto-grants-1988_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04736033

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