1,3-Dichloroacetone → 3-(4-Chloromethyl-thiazol-2-yl)-phenol

HRID 415657Notes

Reaction equation

HRID 415657 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=O.[OH:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=[S:12]>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]1[N:13]=[C:11]([C:10]2[CH:9]=[C:8]([OH:7])[CH:16]=[CH:15][CH:14]=2)[S:12][CH:5]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 27593433-Hydroxybenzene-1-carbothioamide

Product 1

HCID 594027023-(4-Chloromethyl-thiazol-2-yl)-phenolYield 38.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1,3 dichloroacetone (0.42 g, 3.26 mmol) in toluene (5 mL) was added 3-hydroxythiobenzamide (0.25 g, 1.63 mmol) and the reaction mixture was heated at 120° C. for 1 h. After completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness, added water and extracted with EtOAc (×3). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified over silica gel (230-400 M, 10% EtOAc-Hexane) to get the desired product (0.14 g, 38%).

Workup

  1. customAfter completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness
  2. additionadded water
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organics was washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified over silica gel (230-400 M, 10% EtOAc-Hexane)

Sources & evidence

ORD record
ord-78634657f13845739e9cb40da8484591
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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