Methanol → Methyl 4'-acetamidomethyl-2'-methylbiphenyl-4-carboxylate

HRID 399262Notes

Reaction equation

HRID 399262 reaction equation
S(Cl)(Cl)=O.[C:5]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=2)=[C:12]([CH3:25])[CH:11]=1)(=[O:7])[CH3:6].[CH3:26]O>>[C:5]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH3:26])=[O:23])=[CH:18][CH:17]=2)=[C:12]([CH3:25])[CH:11]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 218338034'-Acetamidomethyl-2'-methylbiphenyl-4-carboxylic acid

Product 1

HCID 21833765Methyl 4'-acetamidomethyl-2'-methylbiphenyl-4-carboxylate

Procedure

Thionyl chloride (0.119 ml, 1.63 mmol) was added dropwise to MeOH (5 ml) at 0° C., followed by a solution of 4'-acetamidomethyl-2'-methylbiphenyl-4-carboxylic acid (D1, 0.345 g, 1.22 mmol) in MeOH (10 ml). The mixture was heated under reflux for 1.5 hr and the solvent removed in vacuo. The residue was dissolved in CH2 Cl2 (30 ml) and washed with aq. Na2CO3 followed by water. The organic extract was dried (Na2SO4) and concentrated in vacuo to give a colourless oil which purified by column chromatography on silica gel eluting with EtOAc to give a colourless oil that crystallised on standing (0.242 g, 68%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. customthe solvent removed in vacuo
  4. dissolutionThe residue was dissolved in CH2 Cl2 (30 ml)
  5. washwashed with aq. Na2CO3
  6. extractionThe organic extract
  7. dry with materialwas dried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto give a colourless oil which
  10. custompurified by column chromatography on silica gel eluting with EtOAc
  11. customto give a colourless oil that
  12. customcrystallised

Sources & evidence

ORD record
ord-80c69e0bc5324d1896cab0f7cc83f7ac
Source dataset
uspto-grants-1998_10
Patent number
US05817833

Reaction notes

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