Hydrochloric Acid → HCID 178504596、化合物

HRID 452778

反応式

HRID 452778 の反応式
[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]

参加物

9

反応物 5

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

生成物 1

HCID 178504596HCID 178504596、化合物収率 47%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ebd723acf2724f15b0c884783029fd0e
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

関連ノート

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