Thioanisole → 3-hydroxy-5-[(1-methylethyl)oxy]-N-1,3-thiazol-2-ylbenzamide

HRID 1175850ノート

反応式

HRID 1175850 の反応式
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([O:19]CC2C=CC=CC=2)[CH:18]=1)[C:8]([NH:10][C:11]1[S:12][CH:13]=[CH:14][N:15]=1)=[O:9])[CH3:3].C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[OH:19][C:17]1[CH:16]=[C:7]([CH:6]=[C:5]([O:4][CH:2]([CH3:3])[CH3:1])[CH:18]=1)[C:8]([NH:10][C:11]1[S:12][CH:13]=[CH:14][N:15]=1)=[O:9]

参加物

4

反応物 2

HCID 7520ThioanisoleHCID 53629624HCID 53629624、化合物

生成物 1

HCID 230930393-hydroxy-5-[(1-methylethyl)oxy]-N-1,3-thiazol-2-ylbenzamide収率 84.9%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒2 回

実験手順

3-[(1-Methylethyl)oxy]-5-[(phenylmethyl)oxy]-N-1,3-thiazol-2-ylbenzamide (11.2 g) was dissolved in trifluoroacetic acid (60 mL) and treated with thioanisole (17.8 mL). The mixture was left to stir at ambient temperature for 18 hours before the trifluoroacetic acid was removed in vacuo. The residues were treated with isohexane (100 mL) and the solid filtered off, before being washed with further isohexane (2×20 mL). The solid was dissolved in ethyl acetate (200 mL) and washed with aqueous saturated sodium hydrogen carbonate solution (100 mL). The organics were washed with water (100 mL) and brine (100 mL), and dried (MgSO4) before evaporation in vacuo to afford a solid which was washed with isohexane (200 mL) and dried in vacuo to give the desired compound (7.18 g). 1H NMR δ (d6-DMSO): 1.27 (d, 6H), 4.55 (m, 1H), 6.49 (m, 1H), 7.02 (s, 1H), 7.14 (s, 1H), 7.25 (d, 1H), 7.54 (d, 1H), 9.73 (s, 1H), 12.44 (s, 1H). m/z 279 (M+H)+, 277 (M−H)−

後処理

  1. waitThe mixture was left
  2. customwas removed in vacuo
  3. additionThe residues were treated with isohexane (100 mL)
  4. filtrationthe solid filtered off
  5. washbefore being washed with further isohexane (2×20 mL)
  6. dissolutionThe solid was dissolved in ethyl acetate (200 mL)
  7. washwashed with aqueous saturated sodium hydrogen carbonate solution (100 mL)
  8. washThe organics were washed with water (100 mL) and brine (100 mL)
  9. dry with materialdried (MgSO4)
  10. custombefore evaporation in vacuo
  11. customto afford a solid which
  12. washwas washed with isohexane (200 mL)
  13. customdried in vacuo

出典と根拠

ORDレコード
ord-32b7a796598d4b79904568ec87861282
出典データセット
uspto-grants-2010_11
特許番号
US07842694B2

反応ノート

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