Hydrochloric Acid → Ethyl 7-(4-ethoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate

HRID 413585노트

반응식

HRID 413585 반응식
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13](F)=[C:14]([CH:17]=2)[CH:15]=O)=[CH:6][CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[SH:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)(OCC)OCC.[O-]CC.[Na+].Cl>CN(C)C=O.C(O)(C)C.C(O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[S:25][CH2:26][CH2:27][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:15][C:14]=3[CH:17]=2)=[CH:6][CH:5]=1)[CH3:2]

참가 물질

10

반응물 6

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 11430Potassium CarbonateHCID 271824Ethyl 4-sulfanylbutanoateHCID 2723922Sodium ethoxideHCID 185333825-(4-Ethoxyphenyl)-2-fluorobenzaldehyde

생성물 1

HCID 18533387Ethyl 7-(4-ethoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate수율 57%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 3776Isopropanol용매HCID 6228Dimethylformamide용매

실험 절차

Under an argon atmosphere, 5-(4-ethoxyphenyl)-2-fluorobenzaldehyde (1.0 g) was dissolved in 2 ml of dimethylformamide and 1.17 g of potassium carbonate was added. Thereafter, 1.18 ml of ethyl 4-mercaptobutyrate was added and was stirred at room temperature for 25 hours. After addition of 20 ml of diethyl carbonate and an ethanol solution (2.8 g) of 20% sodium ethoxide, stirring was conducted at room temperature for three hours. During cooling in ice, 21 ml of a 1N hydrochloric acid was added. The mixture was extracted with 50 ml and additional 20 ml of ethyl acetate. The organic layers were combined and washed with 20 ml of water twice. The resulting organic layer was concentrated to yield crystals, which crystals were loosen in 2 ml of isopropyl alcohol added. The crystals were filtered out and were washed with 4 ml of isopropyl ether twice. After vacuum drying, ethyl 7-(4-ethoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate (0.8 g, Yield 57%) was obtained.

후처리

  1. waitwas conducted at room temperature for three hours
  2. temperatureDuring cooling in ice
  3. extractionThe mixture was extracted with 50 ml and additional 20 ml of ethyl acetate
  4. washwashed with 20 ml of water twice
  5. concentrationThe resulting organic layer was concentrated
  6. customto yield crystals, which crystals
  7. additionadded
  8. filtrationThe crystals were filtered out and
  9. washwere washed with 4 ml of isopropyl ether twice
  10. customAfter vacuum drying

출처 및 근거

ORD 기록
ord-e534bfe1a2104df69ebe53303b61702e
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566535B1

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