Hydrochloric Acid → HCID 19786949, compound

HRID 1657025Notes

Reaction equation

HRID 1657025 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)[CH:5]=[N:4][C:3]=1[C:20]#N.CC(C[AlH]CC(C)C)C.[OH2:31].Cl>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)[CH:5]=[N:4][C:3]=1[CH:20]=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 14473663HCID 14473663, compound

Product 1

HCID 19786949HCID 19786949, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-70 °C

Procedure

4.13 g of 5-methyl-1-(3-phenoxyphenyl)-imidazole-4-carbonitrile is dissolved in 200 ml of toluene. At -60° C. to -70° C., 15 ml of Dibah, 1.2 mol in toluene is instilled. It is stirred for 2 hours at -70° C., 2.5 ml of water is instilled at -70° C. and the mixture is allowed to come to room temperature. It is adjusted to pH 4 with 2N hydrochloric acid solution and the mixture is extracted with toluene and ethyl acetate. The organic phases are combined and dried on MgSO4. After purification by column chromatography, 2.46 g (59% of theory) of the title compound is obtained as oil.

Workup

  1. customAt -60° C. to -70° C.
  2. customis instilled at -70° C.
  3. customto come to room temperature
  4. extractionthe mixture is extracted with toluene and ethyl acetate
  5. customdried on MgSO4
  6. customAfter purification by column chromatography, 2.46 g (59% of theory) of the title compound
  7. customis obtained as oil

Sources & evidence

ORD record
ord-d3c4582f2af04469ab2e5e72456bbf43
Source dataset
uspto-grants-1993_10
Patent number
US05256682

Reaction notes

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