2-Aminophenol → Benzoxazole, 2-phenyl-

HRID 2419526Notes

Reaction equation

HRID 2419526 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH2:9]1[CH:18]2[CH:13]([CH2:14]CCC2)[CH2:12][CH2:11][CH2:10]1.C1(C(Cl)(Cl)Cl)C=CC=CC=1>>[C:13]1([C:14]2[O:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)[CH:18]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 58012-AminophenolHCID 7044DecalinHCID 7367Benzotrichloride

Product 1

HCID 70030Benzoxazole, 2-phenyl-

Procedure

16.4 g (0.15 mol) of 2-aminophenol (A) was refluxed together with 75 ml of decaline in the apparatus described under (a). 29.3 g (0.15 mol) of benzotrichloride (B) was added drop by drop over a period of 15 minutes, and the mixture was heated for another 3 hours with gentle refluxing. Then it was suction filtered while hot and concentrated by evaporation under dry. One half was chromatographed through Al2O3 : 7 g of Compound I, melting point 99°-100° C (41% of the theory). Of the remaining half, one gram was sublimed at 140° C and 0.2 mm Hg; 0.8 g of Compound I, melting point 100°-103° C (44% of the theory).

Workup

  1. temperaturethe mixture was heated for another 3 hours with gentle refluxing
  2. filtrationfiltered while hot and
  3. concentrationconcentrated by evaporation
  4. customunder dry
  5. customOne half was chromatographed through Al2O3
  6. customwas sublimed at 140° C

Sources & evidence

ORD record
ord-c27f7429f1604c99a58b464d60ef6264
Source dataset
uspto-grants-1978_08
Patent number
US04107169

Reaction notes

Loading…