Hydrochloric Acid → HCID 54324090, compound

HRID 2165745Notes

Reaction equation

HRID 2165745 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-73b245729ebc4668af65f466fccfca16
Source dataset
uspto-grants-1990_07
Patent number
US04940798

Reaction notes

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