2-Bromo-5-chloro-2,3-dihydro-1H-inden-1-one → HCID 9968928, compound

HRID 1935594Notes

Reaction equation

HRID 1935594 reaction equation
[CH2:1]([S:8][CH2:9][C:10]([NH2:12])=[S:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([Cl:23])[CH:20]=2)[C:15]1=[O:24]>CC(C)=O>[CH2:1]([S:8][CH2:9][C:10]1[S:11][CH:14]2[CH2:22][C:21]3[CH:20]=[C:19]([Cl:23])[CH:18]=[CH:17][C:16]=3[C:15]2([OH:24])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 113340692-Bromo-5-chloro-2,3-dihydro-1H-inden-1-oneHCID 22464923(Benzylsulfanyl)ethanethioamide

Product 1

HCID 9968928HCID 9968928, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

At room temperature, 0.54 g of 2-benzylsulfanyl-thioacetamide were dissolved in 10 ml of dry acetone and mixed with 0.67 g of 2-bromo-5-chlorindan-1-on, and the mixture was stirred at room temperature for 4 h. The resulting precipitate was filtered off with suction, washed with acetone, taken up in ethyl acetate, mixed with saturated sodium bicarbonate solution and extracted twice. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. This synthesis yielded 2-benzylsulfanylmethyl-6-chloro-8,8a-dihydroindeno[1,2-d]thiazol-3a-ol having a melting point of 102-104° C.

Workup

  1. filtrationThe resulting precipitate was filtered off with suction
  2. washwashed with acetone
  3. additionmixed with saturated sodium bicarbonate solution
  4. extractionextracted twice
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e6519afcf2d4a8db9c39c647c52b0f6
Source dataset
uspto-grants-2002_05
Patent number
US06387935B1

Reaction notes

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