Hydrochloric Acid → HCID 20192812, compound

HRID 1589190Notes

Reaction equation

HRID 1589190 reaction equation
[N:1]1([CH2:6][CH2:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=CC=2)=O)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:16]([O-])(=O)[CH3:17].[NH4+:20].[Na].Cl>CO>[N:1]1([CH:6]([C:7]2[CH:8]=[CH:10][CH:15]=[CH:14][CH:13]=2)[CH2:17][CH2:16][NH2:20])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5360545SodiumHCID 134573613-(1H-Imidazol-1-yl)-1-phenylpropan-1-one

Product 1

HCID 20192812HCID 20192812, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6.0 g. of 3-(1H-imidazol-1-yl)propiophenone in 100 ml. of methanol was stirred as 23.1 g. of ammonium acetate, and then 1.35 g. of sodium cyanoborohydrate was added. After 6 days at room temperature, 60 ml. of concentrated hydrochloric acid was added and the solvent was distilled off. The residue was treated with 65 ml. of 10N sodium hydroxide, 25 g. of sodium chloride and 200 ml. of methylene chloride and the layers were separated. The organic layer was washed with water, dried over magnesium sulfate, and concentrated to obtain the desired product as a viscous oil, 5.4 g. When this was reacted with 4-chlorobenzoyl chloride and 4-bromobenzoyl chloride by the procedure of Example 27, the compounds set forth in Table XIX were obtained.

Workup

  1. distillationthe solvent was distilled off
  2. additionThe residue was treated with 65 ml
  3. customof methylene chloride and the layers were separated
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8aff4137633c4ca396e2a5bb6d32c3e6
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

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