Benzyl Bromide → HCID 20359956, compound

HRID 1974034Notes

Reaction equation

HRID 1974034 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 one 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 one 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-ee18e8f7a8f9456a9b9435df4c557c19
Source dataset
uspto-grants-1976_12
Patent number
US04000145

Reaction notes

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