Triethylamine → HCID 9817892, compound

HRID 1596419Notes

Reaction equation

HRID 1596419 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][N:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>CC(C)=O>[Cl:11][C:7]1[CH:6]=[CH:5][C:4]2[C:3]3([OH:12])[N:21]=[C:13]([C:14]4[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=4)[S:20][CH:2]3[CH2:10][C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27237884-PyridinecarbothioamideHCID 113340692-Bromo-5-chloro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 9817892HCID 9817892, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.98 g of 2-bromo-5-chloroindan-1-one and 0.55 g of thioisonicotinamide are dissolved in 40 ml of dry acetone at room temperature and treated with 0.55 ml of triethylamine. The mixture is stirred at room temperature for 2 days. The reaction mixture is concentrated, and the residue is taken up with ethyl acetate and washed twice with water and then twice with satd sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated, and the residue is chromatographed on silica gel using ethyl acetate/n-heptane 10/1. 6-Chloro-2-pyridin-4-yl-8,8a-dihydro-indeno[1,2-d]thiazol-3a-ol of melting point 155-160° C. (dec.) is obtained.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. washwashed twice with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-9f85b2a9a476484684459a5d012b8172
Source dataset
uspto-grants-2001_09
Patent number
US06291486B1

Reaction notes

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