Thioanisole → HCID 59127130, compound

HRID 1990137Notes

Reaction equation

HRID 1990137 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-c50413ef5e284307acbd4d9a588cfbb5
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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