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

HRID 1454039노트

반응식

HRID 1454039 반응식
[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]

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 57528953HCID 57528953, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f99bd8c5acd749bb886ec18a4789ec83
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476742B2

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