Sulfuric Acid → Methyl [2-(3-bromo-4-methylphenyl)-5-methyl-1,3-oxazol-4-yl]acetate

HRID 1454039Notes

Reaction equation

HRID 1454039 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:5]([NH:7][CH:8]([C:14](=[O:16])[CH3:15])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=O.OS(O)(=O)=O>C(OC(=O)C)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[O:16][C:14]([CH3:15])=[C:8]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[N:7]=2)[CH:17]=[CH:18][C:19]=1[CH3:20]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 57528953HCID 57528953, compound

Product 1

HCID 57528961Methyl [2-(3-bromo-4-methylphenyl)-5-methyl-1,3-oxazol-4-yl]acetate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

The total crude material prepared in Example 80 was dissolved in acetic anhydride (25 mL) followed by slow addition of conc. H2SO4 (1 mL). The pot temperature reached 90° C. The reaction was then held at 90° C. for 1 h, cooled, and the acetic anhydride removed in vacuo. The residue was poured into ice water (250 mL) and extracted with EtOAc (300 mL total). The organic layer was then extracted with 1 N HCl (100 mL), saturated NaHCO3 (100 mL) and brine, separated, then dried with NaSO4 and concentrated to afford the title ester (4.6 g). The crude product used in the next step (Example 82).

Workup

  1. customreached 90° C
  2. temperaturecooled
  3. customthe acetic anhydride removed in vacuo
  4. additionThe residue was poured into ice water (250 mL)
  5. extractionextracted with EtOAc (300 mL total)
  6. extractionThe organic layer was then extracted with 1 N HCl (100 mL), saturated NaHCO3 (100 mL) and brine
  7. customseparated
  8. dry with materialdried with NaSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f99bd8c5acd749bb886ec18a4789ec83
Source dataset
uspto-grants-2009_01
Patent number
US07476742B2

Reaction notes

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