Ethanol → HCID 9862361, compound

HRID 2288775Notes

Reaction equation

HRID 2288775 reaction equation
Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:11])[CH:8]=2)[C:3]1=[O:12].[C:13]([NH2:21])(=[S:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1.[CH2:22](O)[CH3:23]>>[Cl:11][C:7]1[CH:6]=[CH:5][C:4]2[C:3]3([O:12][CH2:22][CH3:23])[N:21]=[C:13]([C:14]4[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=4)[S:20][CH:2]3[CH2:10][C:9]=2[CH:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 737155ThionicotinamideHCID 113340692-Bromo-5-chloro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 9862361HCID 9862361, compound

Conditions

Temperature
70 °C

Procedure

1 g of 2-bromo-5-chloroindan-1-one and 622 mg of thionicotinamide are suspended in 10 ml of dry ethanol, and the mixture is stirred at room temperature for 2 h and at 70° C. for 8 h. The reaction mixture is cooled, and the precipitate is filtered off with suction, washed with ethanol, stirred with a little water, again filtered off with suction and dissolved in 50 ml of ethyl acetate. This solution is rendered alkaline with triethylamine, treated with 30 ml of water and the organic phase is separated off, washed with water, dried over magnesium sulfate and concentrated in vacuo, and finally the residue is chromatographed on silica gel using ethyl acetate/n-heptane 1/1. 6-Chloro-3a-ethoxy-2-pyridin-3-yl-8,8a-dihydro-3aH-indeno[1,2-d]thiazole of melting point 89-90° C. is obtained.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationthe precipitate is filtered off with suction
  3. washwashed with ethanol
  4. stirringstirred with a little water
  5. filtrationagain filtered off with suction
  6. dissolutiondissolved in 50 ml of ethyl acetate
  7. additiontreated with 30 ml of water
  8. customthe organic phase is separated off
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuo
  12. customfinally the residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-dd40a12c99b544658b778d31f221795e
Source dataset
uspto-grants-2000_07
Patent number
US06090833

Reaction notes

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