Hydrochloric Acid → HCID 13269992, compound

HRID 1253134Notes

Reaction equation

HRID 1253134 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]([N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)[C:11](=[O:20])[C:12]([CH:15]1[O:19][CH2:18][CH2:17][O:16]1)([CH3:14])[CH3:13].[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]([N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)[CH:11]([OH:20])[C:12]([CH:15]1[O:16][CH2:17][CH2:18][O:19]1)([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 13269990HCID 13269990, compound

Product 1

HCID 13269992HCID 13269992, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

22.9 g (0.06 mol) of 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4-(dioxolan-2-yl)-4-methyl-pentan-3-one are dissolved in 100 ml of methanol, the solution is cooled to 0° C., and 2.95 g (0.078 mol) of sodium borohydride are added in portions. The mixture is stirred for a further 3 hours at room temperature, 15 ml of concentrated hydrochloric acid are added dropwise, stirring is continued for a further 3 hours and 500 ml of saturated sodium bicarbonate solution are then added. The mixture is extracted with 400 ml of methylene chloride, the phases are separated, the organic phase is wshed with twice 100 ml of water, and the solvent is distilled off. The residue is taken up in 150 ml of diisopropyl ether, and the crystals are filtered off under suction. 1-(2,4-Dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4-(dioxolan-2-yl)-4-methyl-pentan-3-ol is obtained as the B form of melting point 178°-81° C., and after approximately 100 ml of diisopropyl ether have been distilled off, 8.9 g of product are obtained as the A form of melting point 95°-100° C.

Workup

  1. stirringstirring
  2. waitis continued for a further 3 hours
  3. extractionThe mixture is extracted with 400 ml of methylene chloride
  4. customthe phases are separated
  5. distillationthe solvent is distilled off
  6. filtrationthe crystals are filtered off under suction

Sources & evidence

ORD record
ord-193a9396f2204b99b8387d8cb3f380ef
Source dataset
uspto-grants-1988_05
Patent number
US04747869

Reaction notes

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