Hydrochloric Acid → HCID 57514645, compound

HRID 515524Notes

Reaction equation

HRID 515524 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=O)[CH:10]([CH3:12])[CH3:11].[Cl:14][CH2:15][C:16]#[N:17]>O1CCOCC1>[Cl:14][CH2:15][C:16]1[N:17]=[C:9]([CH:10]([CH3:12])[CH3:11])[C:4]2[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 122976071-(2-aminophenyl)-2-methylpropan-1-one

Product 1

HCID 57514645HCID 57514645, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dry hydrogen chloride gas is piped through a solution of 2.86 g of 1-(2-amino-phenyl)-2-methyl-propan-1-one and 1.33 ml of chloroacetonitrile in 14 ml dioxane with stirring at ambient temperature for approx. five hours. Then the dioxane is largely distilled off in a water jet vacuum. The honey-like residue is combined with ice water and the resulting suspension is made alkaline with saturated potassium carbonate solution while cooling with an ice bath. The precipitate is suction filtered, washed with water and dried. The crude product is purified by chromatography over a silica gel column with petroleum ether/methylene chloride (8:2 to 0:1) as eluant.

Workup

  1. distillationThen the dioxane is largely distilled off in a water jet vacuum
  2. temperaturewhile cooling with an ice bath
  3. filtrationfiltered
  4. washwashed with water
  5. customdried
  6. customThe crude product is purified by chromatography over a silica gel column with petroleum ether/methylene chloride (8:2 to 0:1) as eluant

Sources & evidence

ORD record
ord-cbd3b6ca6ea74bb4b4acdf8ce97d4c64
Source dataset
uspto-grants-2015_08
Patent number
US09108964B2

Reaction notes

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