p-Toluenesulfonic acid → HCID 67331866, compound

HRID 1886909Notes

Reaction equation

HRID 1886909 reaction equation
FC1C=C(F)C=CC=1C(O[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([CH3:14])=[CH:9][C:8]=1[NH:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24])=O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[C:16]1[O:25][C:7]2[CH:12]=[C:11]([CH3:13])[C:10]([CH3:14])=[CH:9][C:8]=2[N:15]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67331307HCID 67331307, compound

Product 1

HCID 67331866HCID 67331866, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-(2,4-difluorobenzamido)-4,5-dimethylphenyl 2,4-difluorobenzoate (90 mg, 0.22 mmol) and 4-methylbenzenesulfonic acid (82 mg, 0.43 mmol) in xylene (2 mL) was heated at reflux for 16 h. After cooling, the solution was diluted with ethyl acetate and washed with aqueous sodium bicarbonate solution followed by brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 1:15 v/v to afford 36 mg (64%) of the title compound (LCMS RT=7.81 min, MH+ 260.0)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. temperatureAfter cooling
  4. washwashed with aqueous sodium bicarbonate solution
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. customevaporated
  7. customThe resulting solid was purified by column chromatography
  8. washeluting with ethyl acetate/hexanes 1:15 v/v

Sources & evidence

ORD record
ord-d84f5ccb28284ee7bdf7536bb0adaa70
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

Loading…