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Tetrahydrofuran → 2-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanthioamide

HRID 1655542
ノート
印刷プレビュー

反応式

HRID 1655542 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:35]=[CH:34][C:16]([O:17][CH:18]([CH3:33])[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)=O)=[CH:15][CH:14]=1)[CH:6]=[N:5]2.C1COCC1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:42]>O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:35]=[CH:34][C:16]([O:17][CH:18]([CH3:33])[C:19](=[S:42])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)=[CH:15][CH:14]=1)[CH:6]=[N:5]2
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 8028TetrahydrofuranHCID 14817Phosphorus sulfide (P2S5)HCID 197926992-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide

生成物 1

HCID 197926792-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanthioamide

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A mixture of 2.0 g (4.1 mmol) of 2-(4-((6-fluoro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide and 40 ml of dry THF in a 100 ml flask was placed in a water-filled ultrasonic bath. Phosphorous pentasulfide (0.22 g) was added and the mixture sonicated while maintaining the reaction temperature below 40° C. by occasional addition of ice to the water bath. Additional P2S5 (1.76 g) was added in portions at 20 minute intervals over the next hour. Sonication was continued for an additional 2 hours and the mixture then filtered and the solid washed well with methylene chloride. The combined filtrates were treated with charcoal, filtered and evaporated to dryness. The residue was purified first by chromatography over silica gel, eluting with CH2Cl2, and then by preparative scale HPLC, eluting with 85:15 hexane: acetone. This left 1.1 g (53 percent of theoretical) of the above-named product as a yellow glassy solid. (Compound 34)

後処理

  1. additionfilled ultrasonic bath
  2. customthe mixture sonicated
  3. temperaturewhile maintaining the reaction temperature below 40° C.
  4. customSonication
  5. filtrationthe mixture then filtered
  6. washthe solid washed well with methylene chloride
  7. additionThe combined filtrates were treated with charcoal
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was purified first by chromatography over silica gel
  11. washeluting with CH2Cl2
  12. washby preparative scale HPLC, eluting with 85:15 hexane

出典と根拠

ORDレコード
ord-91b9e493e41d49a4b0a84f1c7bd934bf
出典データセット
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05250690

反応ノート

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