Acetic Acid → HCID 18987046, compound

HRID 2396417Notes

Reaction equation

HRID 2396417 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.CO[CH:14]1[CH2:18][CH2:17][CH:16](OC)O1.C(O)(=O)C>C(Cl)Cl>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]([CH3:10])=[N:7][C:6]=3[CH:11]=2)[CH:14]=[CH:18][CH:17]=[CH:16]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 7379202-Methyl-1,3-benzoxazol-5-amine

Product 1

HCID 18987046HCID 18987046, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Amino-2-methylbenzoxazole (30.0 g, 0,203 mol) and 2,5-dimethoxytetrahydrofuran (30.0 g, 0.227 mol) were combined with 90 mL of acetic acid and the solution was heated at reflux for 1 hr. The mixture was evaporated to a red slurry and mixed with hexane to give a dark solid. The solid was dissolved in methylene chloride and extracted with basic water. The organic phase was removed, dried, and evaporated to a brown solid. Recrystallization from hexane/heptane afforded 18 g (45% yield) of product, m.p. 115°-121° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 1 hr
  3. customThe mixture was evaporated to a red slurry
  4. additionmixed with hexane
  5. customto give a dark solid
  6. extractionextracted with basic water
  7. customThe organic phase was removed
  8. customdried
  9. customevaporated to a brown solid
  10. customRecrystallization from hexane/heptane

Sources & evidence

ORD record
ord-7a2048f413ca42308a2a02b8676096b2
Source dataset
uspto-grants-1996_02
Patent number
US05492802

Reaction notes

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