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

HRID 2102779Notes

Reaction equation

HRID 2102779 reaction equation
Br[CH:2]1[C:7](=O)[CH2:6][CH2:5][CH2:4][C:3]1=[O:9].[C:10]([NH2:13])(=[S:12])[CH3:11]>N1C=CC=CC=1>[CH3:11][C:10]1[S:12][C:2]2[C:3](=[O:9])[CH2:4][CH2:5][CH2:6][C:7]=2[N:13]=1

Participants

4

Reactant 2

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

Product 1

HCID 149133692-Methyl-5,6-dihydrobenzo[d]thiazol-7(4H)-oneYield 40%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

w To a solution of 2-bromo-cyclohexane-1,3-dione (20 g, 0.105 mol) in pyridine (150 mL) was added thioacetamide (7.9 g, 0.105 mol) and the mixture was stirred at 50° C. After 16 h the solvent was removed under vacuum. 10% aq NaCl solution (150 mL) was added and the product was extracted with CH2Cl2 (4×100 mL). The organic extracts were washed with additional 10% aq NaCl solution (2×100 mL) before being dried, filtered, and concentrated under vacuum. The dark viscous oil obtained was purified using a Kugelrohr distillation unit to afford the product as a yellow oil (6.97 g, 40%): 1H-NMR (CDCl3): δ 3.02 (t, 2H, J 6.1, CH2), 2.75 (s, 3H, CH3), 2.61 (t, 2H, J 6.1, CH2), 2.21 (qu, 2H, J 6.1, CH2). 13C-NMR (CDCl3): δ 192.1, 173.3, 166.8, 130.9, 37.8, 27.1, 23.1, 20.0. MS (ESI+): m/z 168.03 (M+H)+.

Workup

  1. customAfter 16 h the solvent was removed under vacuum
  2. addition10% aq NaCl solution (150 mL) was added
  3. extractionthe product was extracted with CH2Cl2 (4×100 mL)
  4. washThe organic extracts were washed with additional 10% aq NaCl solution (2×100 mL)
  5. custombefore being dried
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe dark viscous oil obtained
  9. customwas purified
  10. distillationa Kugelrohr distillation unit

Sources & evidence

ORD record
ord-d427847699f2427ebbc47512c662a06d
Source dataset
uspto-grants-2009_08
Patent number
US07576091B2

Reaction notes

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