Benzoyl chloride → 6-Methyl-2-phenyl-1,3-benzoxazole

HRID 1658079Notes

Reaction equation

HRID 1658079 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:18])=[CH:15][C:16]=1O>N1C=CC=CC=1>[CH3:18][C:14]1[CH:13]=[CH:12][C:11]2[N:10]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[O:8][C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 760822-Amino-5-methylphenol

Product 1

HCID 123707806-Methyl-2-phenyl-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzoyl chloride (79 ml) was slowly added to a stirred suspension of 6-amino-m-cresol (83 gm) in pyridine (600 ml). The temperature was kept below 5°C. The solution was heated under reflux for 2 hr., then was evaporated to dryness to give an oil. This oil was extracted with aqueous 2N sodium hydroxide solution. The aqueous layer was made acid with concentrated hydrochloric acid. The solid, N-(2'-hydroxy-4'-methylbenzanilide), m.p. 170°C, was filtered off. This product was heated until no more water was evolved. The resulting liquid was allowed to cool and the solid produced was powdered and taken up in petroleum ether. The solution was treated with carbon and the filtrate evaporated to dryness to yield 6-methyl-2-phenylbenzoxazole, m.p. 93°C.

Workup

  1. customwas kept below 5°C
  2. temperatureThe solution was heated
  3. temperatureunder reflux for 2 hr
  4. custom, then was evaporated to dryness
  5. customto give an oil
  6. extractionThis oil was extracted with aqueous 2N sodium hydroxide solution
  7. filtrationThe solid, N-(2'-hydroxy-4'-methylbenzanilide), m.p. 170°C, was filtered off
  8. temperatureThis product was heated until no more water
  9. temperatureto cool
  10. customthe solid produced
  11. additionThe solution was treated with carbon
  12. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-21ff61265e6d4aa6b28783741b1064f8
Source dataset
uspto-grants-1976_06
Patent number
US03962441

Reaction notes

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