Thioanisole → 3-Hydroxy-5-[(propan-2-yl)oxy]-N-(1,3-thiazol-2-yl)benzamide

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)−

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

ORD record

ord-2cc563c89a5e412e8e2cbe828616926a

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07642259B2