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

HRID 1175850노트

반응식

HRID 1175850 반응식
[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]

참가 물질

4

반응물 2

HCID 7520ThioanisoleHCID 53629624HCID 53629624, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매2회

실험 절차

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)−

후처리

  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

출처 및 근거

ORD 기록
ord-32b7a796598d4b79904568ec87861282
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842694B2

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