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Hydrochloric Acid → 7-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzo[1,2,5]thiadiazole-4-carboxylic acid

HRID 536423
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HRID 536423 반응식
C[O:2][C:3]([C:5]1[C:10]2=[N:11][S:12][N:13]=[C:9]2[C:8]([C:14]2[CH2:18][C:17]([C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)([C:19]([F:22])([F:21])[F:20])[O:16][N:15]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].Cl>O1CCCC1.C(OCC)(=O)C>[Cl:29][C:27]1[CH:28]=[C:23]([C:17]2([C:19]([F:22])([F:20])[F:21])[O:16][N:15]=[C:14]([C:8]3[C:9]4[C:10](=[N:11][S:12][N:13]=4)[C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=3)[CH2:18]2)[CH:24]=[C:25]([Cl:30])[CH:26]=1
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참가 물질

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반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 584979897-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzo[1,2,5]thiadiazole-4-carboxylic acid methyl ester

생성물 1

HCID 584979767-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzo[1,2,5]thiadiazole-4-carboxylic acid수율 33.1%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 7-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazol-3-yl]-benzo[1,2,5]thiadiazole-4-carboxylic acid methyl ester (4.01 g) (Example I7) in tetrahydrofuran (30 ml) was added aqueous sodium hydroxide (1M) (25.3 ml). The reaction mixture was stirred at ambient temperature for 1.5 hours. Aqueous hydrochloric acid (1M) (100 ml) was added and the mixture diluted with ethyl acetate (150 ml). After separation of the layers, the aqueous layer was extracted with ethyl acetate (2×75 ml). The combined organic layers were washed with water (75 ml) and brine (75 ml), dried over sodium sulfate and concentrated. The residue was purified by column chromatography (dichloromethane/methanol) to give 7-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzo[1,2,5]thiadiazole-4-carboxylic acid (1.29 g) as yellow solid. 1H-NMR (DMSO-d6, 400 MHz): 13.67 (bs, 1H), 8.37-7.26 (m, 5H), 4.76 (d, 1H), 4.53 (d, 1H) ppm.

후처리

  1. customAfter separation of the layers
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×75 ml)
  3. washThe combined organic layers were washed with water (75 ml) and brine (75 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-fc48ed31853c4391ad1effb3cfac59bb
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08859592B2

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