Thioanisole → HCID 59127130, compound

HRID 1011685Notes

Reaction equation

HRID 1011685 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([O:20]CC2C=CC=CC=2)[CH:19]=1)[C:8]([NH:10][C:11]1[S:15][N:14]=[C:13]([CH3:16])[N:12]=1)=[O:9])[CH3:3].C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[OH:20][C:18]1[CH:17]=[C:7]([CH:6]=[C:5]([O:4][CH:2]([CH3:3])[CH3:1])[CH:19]=1)[C:8]([NH:10][C:11]1[S:15][N:14]=[C:13]([CH3:16])[N:12]=1)=[O:9]

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 53629626HCID 53629626, compound

Product 1

HCID 59127130HCID 59127130, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-[(1-methylethyl)oxy]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-5-[(phenylmethyl)oxy]benzamide (33 g, 86 mmol), trifluoroacetic acid (160 mL) and thioanisole (50.5 mL) was stirred at ambient temperature for 48 hours. The TFA was removed in vacuo and the residue poured into saturated sodium bicarbonate solution (300 mL) and extracted into ethyl acetate (twice). The combined organic extracts were washed with brine, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was triturated with DCM and washed with 5% ethyl acetate in isohexane to give the desired compound (12.8 g). 1H NMR δ (d6-DMSO): 1.31 (d, 6H), 2.51 (s, 3H), 4.67 (sept, 1H), 6.58 (s, 1H), 7.08 (s, 1H), 7.24 (s, 1H), 9.88 (s, 1H), 13.25 (brs, 1H). m/z 294 (M+H)+

Workup

  1. customThe TFA was removed in vacuo
  2. additionthe residue poured into saturated sodium bicarbonate solution (300 mL)
  3. extractionextracted into ethyl acetate (twice)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was triturated with DCM
  9. washwashed with 5% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-7690e8d5c8734224974f9d886122fb1c
Source dataset
uspto-grants-2011_07
Patent number
US07977328B2

Reaction notes

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