Potassium Hydroxide → 9-Bromo-5,6-dihydrobenzo[F]imidazo[1,2-D][1,4]oxazepine-2-carboxylic acid

HRID 624639Notes

Reaction equation

HRID 624639 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:18][CH2:19][OH:20])[CH:10]=[C:11]([C:13]([O:15]CC)=[O:14])[N:12]=2)=[C:4](F)[CH:3]=1.[OH-].[K+].Cl.C[N+](CCCC)(CCCC)CCCC>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[N:9]([CH:10]=[C:11]([C:13]([OH:15])=[O:14])[N:12]=3)[CH2:18][CH2:19][O:20][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 567953Methyl tributylammonium hydrochlorideHCID 85472880Ethyl 2-(4-bromo-2-fluorophenyl)-1-(2-hydroxyethyl)-1H-imidazole-4-carboxylate

Product 1

HCID 582043519-Bromo-5,6-dihydrobenzo[F]imidazo[1,2-D][1,4]oxazepine-2-carboxylic acid

Procedure

Ethyl 2-(4-bromo-2-fluorophenyl)-1-(2-hydroxyethyl)-1H-imidazole-4-carboxylate 27, potassium hydroxide and methyl tributylammonium hydrochloride were reacted at 65° C., cooled, and concentrated. The mixture was dissolved in ethanol and water to crystallize 28.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionThe mixture was dissolved in ethanol
  4. customwater to crystallize 28

Sources & evidence

ORD record
ord-2f7ef24dd44e4704aec6b0b15e466578
Source dataset
uspto-grants-2016_04
Patent number
US09303043B2

Reaction notes

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