Hydrochloric Acid → HCID 54324090, compound

HRID 568312Notes

Reaction equation

HRID 568312 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:23])([CH3:22])[C:10](=[O:21])[C:11]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:12]N(C)C)=[CH:4][CH:3]=1.[CH2:24]([Mg]Br)[CH2:25][CH3:26].Cl>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([CH3:22])([CH3:23])[C:10](=[O:21])[C:11]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:12][CH2:24][CH2:25][CH3:26])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 53860039HCID 53860039, compoundHCID 178455851HCID 178455851, compound

Product 1

HCID 54324090HCID 54324090, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

49.9 g (0.15 mol) of 1-(4-chlorophenyl)-2,2-dimethyl-5-dimethylamino-4-(1,2,4-triazol-1-yl)-4-penten-3-one are dissolved in 750 ml of ether, and a solution of 33.9 g (0.23 mol) of n-propyl-magnesium bromide in 100 ml of ether is added dropwise at -20° C. The reaction mixture is subsequently stirred for 1.5 hours, during which it warms to room temperature. The reaction mixture is adjusted to a pH value of 7 to 8 with dilute hydrochloric acid. The organic phase is then separated off, washed with water, dried over sodium sulphate and concentrated. The residue is purified by column chromatography (silica gel; ethyl acetate/cyclohexane=3:1). 30.1 g (60.5% of theory) of 1-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-4-octen-3-one of refractive index nD20 1.5429 are obtained.

Workup

  1. customwarms to room temperature
  2. customThe organic phase is then separated off
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography (silica gel; ethyl acetate/cyclohexane=3:1)

Sources & evidence

ORD record
ord-5c86b09bac89485f8e704dd8fbbf0861
Source dataset
uspto-grants-1988_03
Patent number
US04728356

Reaction notes

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