Benzyl Bromide → HCID 20359956, compound

HRID 1657665Notes

Reaction equation

HRID 1657665 reaction equation
[OH:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]=[C:3]1[C:12]([F:15])([F:14])[F:13].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:16]([O:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]=[C:3]1[C:12]([F:15])([F:14])[F:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 30824181-Hydroxyfluromidine

Product 1

HCID 20359956HCID 20359956, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Hydroxy-6-chloro-2 -(trifluoromethyl)-1H-imidazo-(4,5-b)pyridine (5 grams), 10 milliliters of benzyl bromide, 20 grams of anhydrous potassium carbonate, and 100 milliliters of ethanol were mixed, heated to reflux, and refluxed for 1 hour. The reaction mixture was then filtered, evaporated under vacuum, and extracted with diethyl ether. The extract was filtered and evaporated under vacuum yielding a dark oil which on standing crystallized as the desired 1-benzyloxy-6-chloro-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine. It was recrystallized from a mixture of acetone and petroleum ether boiling at 60°-80°C., m.p., 107°-09°C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperaturerefluxed for 1 hour
  4. filtrationThe reaction mixture was then filtered
  5. customevaporated under vacuum
  6. extractionextracted with diethyl ether
  7. filtrationThe extract was filtered
  8. customevaporated under vacuum
  9. customyielding a dark oil which
  10. customon standing crystallized as the desired 1-benzyloxy-6-chloro-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine
  11. customIt was recrystallized from a mixture of acetone and petroleum ether boiling at 60°-80°C., m.p., 107°-09°C

Sources & evidence

ORD record
ord-537166d7754545ffaa2c89e8fba96a33
Source dataset
uspto-grants-1976_06
Patent number
US03961937

Reaction notes

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