Ammonium Hydroxide → 2-(2,4-Dichlorophenyl)-1-(thiazol-5-yl)propan-2-ol

HRID 345431Notes

Reaction equation

HRID 345431 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:18])([CH3:17])[CH2:10][C:11]1[S:15][C:14](Cl)=[N:13][CH:12]=1.[OH-].[NH4+]>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:18])([CH3:17])[CH2:10][C:11]1[S:15][CH:14]=[N:13][CH:12]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 199924352-(2,4-Dichlorophenyl)-1-(2-chlorothiazol-5-yl)propan-2-ol

Product 1

HCID 199924342-(2,4-Dichlorophenyl)-1-(thiazol-5-yl)propan-2-olYield 56%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

The 2-(2,4-dichlorophenyl)-1-(2-chlorothiazol-5-yl)propan-2-ol (6.4 g) obtained in Example 1 was dissolved in acetic acid (80 ml) and the mixture brought to reflux whereupon zinc dust (3.5 g) was added and the mixture was stirred under reflux for a further 2 hours and then cooled. Dilute ammonium hydroxide solution was added until the reaction mixture was basic and the mixture was then extracted into ethyl acetate (2×200 ml). The combined extract was washed with brine (50 ml), dried and then concentrated under reduced pressure. Flash chromatography of the residue on a silica gel column using petroleum ether-ethyl acetate as eluant gave 2-(2,4-dichlorophenyl)-1-(thiazol-5-yl)propan-2-ol (3.2 g) as a white solid, m.pt. 164° C.

Workup

  1. additionwas added
  2. temperatureunder reflux for a further 2 hours
  3. temperaturecooled
  4. extractionthe mixture was then extracted into ethyl acetate (2×200 ml)
  5. extractionThe combined extract
  6. washwas washed with brine (50 ml)
  7. customdried
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-29ab886adec14a78b2b02a7e641ab434
Source dataset
uspto-grants-1991_10
Patent number
US05057529

Reaction notes

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