Thioacetamide → 2-Methyl-5,6-dihydrobenzo[d]thiazol-7(4H)-one

HRID 2371047Notes

Reaction equation

HRID 2371047 reaction equation
[C:1](=[S:4])([NH2:3])[CH3:2].Br[CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]1=O>C(O)C>[CH3:2][C:1]1[S:4][C:10]2[C:11](=[O:12])[CH2:6][CH2:7][CH2:8][C:9]=2[N:3]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 27704762-Bromocyclohexane-1,3-dione

Product 1

HCID 149133692-Methyl-5,6-dihydrobenzo[d]thiazol-7(4H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethanethioamide (0.75 g, 10 mmol) in ethanol (20 mL) at room temperature was added 2-bromocyclohexane-1,3-dione (1.9 g, 10 mmol) in portions. The reaction solution was refluxed for 2 hours while stirring. After removal of solvents, the residue was diluted with water and washed with diethyl ether. The separated aqueous layer was basified with sodium carbonate solution. The resulting solid was collected by vacuum filtration, rinsed with water. The solid was suspended in methanol and followed by evaporation to dryness to produce the title compound.

Workup

  1. temperatureThe reaction solution was refluxed for 2 hours
  2. customAfter removal of solvents
  3. additionthe residue was diluted with water
  4. washwashed with diethyl ether
  5. filtrationThe resulting solid was collected by vacuum filtration
  6. washrinsed with water
  7. customfollowed by evaporation to dryness

Sources & evidence

ORD record
ord-ce6dc72c650a4d18bcf495da9bdd852e
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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