Acetylglycine → 2-Methyl-4-(3,5-dimethyl-4-(4-methoxy-3-(6-methoxy-3-pyridylmethyl)-phenoxy)-benzal)-5-oxazolone

HRID 35286

Reaction equation

HRID 35286 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH:24]=O)=[CH:19][C:18]=3[CH3:26])[CH:13]=[CH:12][C:11]=2[O:27][CH3:28])=[CH:5][N:4]=1.[C:29]([NH:32][CH2:33][C:34]([OH:36])=[O:35])(=O)[CH3:30].C([O-])(=O)C.[Na+]>C(OC(=O)C)(=O)C>[CH3:30][C:29]1[O:36][C:34](=[O:35])[C:33](=[CH:24][C:20]2[CH:21]=[C:22]([CH3:23])[C:17]([O:16][C:14]3[CH:13]=[CH:12][C:11]([O:27][CH3:28])=[C:10]([CH2:9][C:6]4[CH:5]=[N:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[CH:15]=3)=[C:18]([CH3:26])[CH:19]=2)[N:32]=1

Participants

5

Reactant 3

HCID 10972AcetylglycineHCID 517045Sodium AcetateHCID 146735552-Methoxy-5-(2-methoxy-5-(2,6-dimethyl-4-formylphenoxy)benzyl)-pyridine

Product 1

HCID 542513612-Methyl-4-(3,5-dimethyl-4-(4-methoxy-3-(6-methoxy-3-pyridylmethyl)-phenoxy)-benzal)-5-oxazoloneYield 64%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

2-Methoxy-5-(2-methoxy-5-(2,6-dimethyl-4-formylphenoxy)benzyl)-pyridine (10.84 g), N-acetylglycine (5.38 g), sodium acetate (3.77 g) and acetic anhydride (70 ml) were stirred at 100±5°, (oil bath temperature) for 24 hours. The solution was cooled and evaporated to leave a brown gum which was triturated with water, then with methanol to afford 2-methyl-4-(3,5-dimethyl-4-(4-methoxy-3-(6-methoxy-3-pyridylmethyl)-phenoxy)-benzal)-5-oxazolone as a yellow solid (8.27 g, 64%), m.p. 164°-165°.

Workup

  1. temperatureThe solution was cooled
  2. customevaporated
  3. customto leave a brown gum which
  4. customwas triturated with water

Sources & evidence

ORD record
ord-f276d13413624499a24384605d8576bb
Source dataset
uspto-grants-1988_08
Patent number
US04766121

Linked notes

Loading…