Thioacetamide → HCID 9839216, compound

HRID 2269298Notes

Reaction equation

HRID 2269298 reaction equation
Br[CH:2]1CC2C(=CC=C(C3C=CC=C(Cl)C=3)C=2)C1=O.C(N)(=S)C.Br.[Cl:24][C:25]1[CH:26]=[C:27]([C:31]2[CH:43]=[CH:42][C:41]3[C:36]4([OH:44])[N:37]=[C:38]([CH3:40])[S:39][CH:35]4[CH2:34][C:33]=3[CH:32]=2)[CH:28]=[CH:29][CH:30]=1>CC(C)=O>[Cl:24][C:25]1[CH:26]=[C:27]([C:31]2[CH:43]=[CH:42][C:41]3[C:36]4[N:37]=[C:38]([CH3:40])[S:39][C:35]=4[CH2:34][C:33]=3[CH:32]=2)[CH:28]=[CH:29][CH:30]=1.[Cl:24][C:25]1[CH:26]=[C:27]([C:31]2[CH:43]=[CH:42][C:41]3[C:36]4([O:44][CH3:2])[N:37]=[C:38]([CH3:40])[S:39][CH:35]4[CH2:34][C:33]=3[CH:32]=2)[CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 2723949ThioacetamideHCID 15460158HCID 15460158, compoundHCID 18347152HCID 18347152, compound

Product 2

HCID 9839216HCID 9839216, compoundHCID 18347157HCID 18347157, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

321 mg of 2-bromo-5-(3-chlorophenyl)indan-1-one are dissolved with 83 mg of thioacetamide in 10 ml of dry acetone and stirred at 0° C. for 5 h. The precipitate consisting of 6-(3-chlorophenyl)-2-methyl-8,8a-dihydroindeno[1,2-d]thiazol-3a-ol hydrobromide is filtered off with suction, washed with acetone, dried in vacuo and then dissolved in 20 ml of dry methanol. The solution is left to stand at room temperature for 2 weeks. It is made basic with triethylamine, concentrated and purified on silica gel with ethyl acetate/n-heptane 1/1. 6-(3-Chlorophenyl)-2-methyl-8H-indeno[1,2-d]thiazole is obtained with a melting point of 111-112° C. in addition to 6-(3-chlorophenyl)-3a-methoxy-2-methyl-8,8a-dihydro-3aH-indeno[1,2-d]thiazole with a melting point of 80-82° C.

Workup

  1. filtrationis filtered off with suction
  2. washwashed with acetone
  3. customdried in vacuo
  4. dissolutiondissolved in 20 ml of dry methanol
  5. waitThe solution is left
  6. waitto stand at room temperature for 2 weeks
  7. concentrationconcentrated
  8. custompurified on silica gel with ethyl acetate/n-heptane 1/1

Sources & evidence

ORD record
ord-9ea48fa26b0c46eb9f395ea66474bff1
Source dataset
uspto-grants-2001_12
Patent number
US06329407B1

Reaction notes

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