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Pyridine → 9-(4-Chloro-5-ethylsulfonylamino-2-fluorophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione

HRID 1164712
ノート
印刷プレビュー

反応式

HRID 1164712 の反応式
[NH2:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]([F:19])=[C:6]([N:8]=[C:9]2[N:17]3[N:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)[C:11](=[S:18])[S:10]2)[CH:7]=1.[CH2:21]([S:23](Cl)(=[O:25])=[O:24])[CH3:22].N1C=CC=CC=1>C(Cl)Cl>[Cl:20][C:3]1[C:2]([NH:1][S:23]([CH2:21][CH3:22])(=[O:25])=[O:24])=[CH:7][C:6]([N:8]=[C:9]2[N:17]3[N:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)[C:11](=[S:18])[S:10]2)=[C:5]([F:19])[CH:4]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 146229579-(5-Amino-4-chloro-2-fluorophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione

生成物 1

HCID 146229589-(4-Chloro-5-ethylsulfonylamino-2-fluorophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione収率 20.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

A mixture of 0.45 g (0.0014 mole) of 9-(5-amino-4-chloro-2-fluorophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione, 0.18 g (0.0014 mole) of ethanesulfonyl chloride, and 0.22 g (0.027 mole) of pyridine in approximately 30 mL of methylene chloride was stirred at room temperature for two days. The reaction mixture was heated at 26° C. for approximately 24 hours, then at reflux for 36 hours. The solvent was evaporated from the mixture leaving an oily residue. The residue was washed with an aqueous, 10% hydrochloric acid solution. The washed residue crystallized upon standing and was recrystallized from ethyl acetate and n-heptane to give 0.12 g of 9-(4-chloro-5-ethylsulfonylamino-2-fluorophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione, mp 146°-148° C., Compound 11 of Table 1.

後処理

  1. temperatureThe reaction mixture was heated at 26° C. for approximately 24 hours
  2. temperatureat reflux for 36 hours
  3. customThe solvent was evaporated from the mixture
  4. customleaving an oily residue
  5. washThe residue was washed with an aqueous, 10% hydrochloric acid solution
  6. customThe washed residue crystallized
  7. customwas recrystallized from ethyl acetate and n-heptane

出典と根拠

ORDレコード
ord-7832c4cc9b2749c4b238a37e6e2c5c37
出典データセット
uspto-grants-1990_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04906281

反応ノート

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