Methanol → HCID 18440833, compound

HRID 1782528Notes

Reaction equation

HRID 1782528 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:10]1(C)C=[CH:14][CH:13]=[CH:12][CH:11]=1.C[OH:18]>>[CH3:10][C:11]1[N:9]=[C:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[S:8][C:12]=1[CH2:13][CH2:14][OH:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 1140TolueneHCID 737155Thionicotinamide

Product 1

HCID 18440833HCID 18440833, compoundYield 31%

Conditions

Temperature
80 °C

Procedure

2-(4-Methyl-2-pyridin-3-yl-thiazole-5-yl)-ethanol was prepared according to the general procedure presented hereinabove, by adding 20 grams (0.145 moles) of thionicotinamide (purchased from Acros, Belgium) to 200 ml of dry toluene, followed by addition of 26 grams (0.145 moles) of ACP over a time period of 20 minutes. The reaction mixture heated for 24 hours at 80° C. and thereafter about 180 ml of toluene were removed by evaporation. 100 ml of water and 20 ml of HCl solution (32%) were added and reflux was continued for 1 hour at 90° C. The organic phase was then removed by washing with chloroform and the aqueous phase was turned basic (pH 8-9) using a 5 N solution of NaOH. The 2-(4-methyl-2-pyridin-3-yl-thiazole-5-yl)-ethanol was extracted with three portions of 100 ml of chloroform and the combined extracts were dried over sodium sulfate. The chloroform was thereafter removed and 5 the residue was purified by liquid chromatography, using a mixture of 9:1 ethyl acetate:methanol as eluent, to give 10 grams (31% yield) of the 2-(4-methyl-2-pyridin-3-yl-thiazole-5-yl)-ethanol product as a violet-brown powder.

Workup

  1. custom2-(4-Methyl-2-pyridin-3-yl-thiazole-5-yl)-ethanol was prepared
  2. additionfollowed by addition of 26 grams (0.145 moles) of ACP over a time period of 20 minutes
  3. customabout 180 ml of toluene were removed by evaporation
  4. addition100 ml of water and 20 ml of HCl solution (32%) were added
  5. temperaturereflux
  6. customThe organic phase was then removed
  7. washby washing with chloroform
  8. extractionThe 2-(4-methyl-2-pyridin-3-yl-thiazole-5-yl)-ethanol was extracted with three portions of 100 ml of chloroform
  9. dry with materialthe combined extracts were dried over sodium sulfate
  10. customThe chloroform was thereafter removed
  11. custom5 the residue was purified by liquid chromatography
  12. additiona mixture of 9:1 ethyl acetate

Sources & evidence

ORD record
ord-88c60881f4094a009dcda25f699fbe6a
Source dataset
uspto-grants-2009_03
Patent number
US07498445B2

Reaction notes

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