HCID 22618319, compound → Benzoxazole

HRID 1377542Notes

Reaction equation

HRID 1377542 reaction equation
Br[C:2]1[CH:7]=[C:6](Cl)[CH:5]=[C:4]([N:9](C2C=CC(OC)=C(OC3CCCC3)C=2)[C:10](=O)C)[C:3]=1[OH:27]>C1(C)C=CC=CC=1.P(Cl)(Cl)(Cl)=O>[O:27]1[C:3]2[CH:2]=[CH:7][CH:6]=[CH:5][C:4]=2[N:9]=[CH:10]1

Participants

4

Reactant 1

HCID 22618319HCID 22618319, compound

Product 1

HCID 9228BenzoxazoleYield 261.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

A suspension of 32.9 g (72.4 mM) of the 2-Bromo-4-chloro-6-(3-cyclopentyloxy-4-methoxy-phenyl-acetylamino)-phenol in 400 ml of toluene and 39.7 ml (434 mM) of phosphorus oxychloride was refluxed for 1.5 hr. Some solid material was filtered off and the filtrate evaporated to dryness in vacuo. The honey-like residue was suspended in 200 ml of sodium bicarbonate solution for 1 hr. The solid was collected, washed and dried at 25° C. to give 22.53 g (71.2%) of crude benzoxazole.

Workup

  1. temperaturewas refluxed for 1.5 hr
  2. filtrationSome solid material was filtered off
  3. customthe filtrate evaporated to dryness in vacuo
  4. customThe solid was collected
  5. washwashed
  6. customdried at 25° C.

Sources & evidence

ORD record
ord-906400c3a9724dccbe8d60f5059285a6
Source dataset
uspto-grants-1997_09
Patent number
US05665737

Reaction notes

Loading…