Hydrochloric Acid → HCID 178504596, 화합물

HRID 452778

반응식

HRID 452778 반응식
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[CH:15]=[C:16]([C:19]([O:21]C)=O)[CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)=[CH:6][CH:5]=1)=[O:3].O.[NH2:24][NH2:25].[C:26](=[S:28])=S.C(N(CC)CC)C.Cl>CO.C(O)C.O>[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[CH:15]=[C:16]([C:19]4[O:21][C:26]([SH:28])=[N:25][N:24]=4)[CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)=[CH:6][CH:5]=1)=[O:3]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 44482291Methyl 3-[4-(methylsulfinyl)phenyl]-1-benzofuran-5-carboxylate

생성물 1

HCID 178504596HCID 178504596, 화합물수율 47%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of methyl 3-[4-(methylsulfinyl)phenyl]-1-benzofuran-5-carboxylate (2.23 g, 7.10 mmol) and hydrazine monohydrate (1.76 mL, 36.3 mmol) in methanol (25 mL) was heated under reflux for 4 days. After cooling, the reaction mixture was concentrated under reduced pressure, and a solution of the obtained residue, carbon disulfide (1.28 mL, 21.3 mmol) and triethylamine (1.19 mL, 8.52 mmol) in ethanol (30 mL) was heated under reflux for 4 hr. After cooling, the reaction mixture was poured into water, and the mixture was acidified with 1M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from tetrahydrofuran to give the title compound (1.19 g, yield 47%) as pale-yellow crystals.

후처리

  1. temperatureunder reflux for 4 days
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. temperatureunder reflux for 4 hr
  5. temperatureAfter cooling
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized from tetrahydrofuran

출처 및 근거

ORD 기록
ord-ebd723acf2724f15b0c884783029fd0e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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