Thioacetamide → Ethyl 2-methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-6-carboxylate

HRID 574977Notes

Reaction equation

HRID 574977 reaction equation
Br[CH:2]1[C:7](=O)[CH2:6][CH2:5][CH:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3]1.[C:14](=[S:17])([NH2:16])[CH3:15]>CN(C)C=O>[CH3:15][C:14]1[S:17][C:2]2[CH2:3][CH:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:6][C:7]=2[N:16]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 12917737Ethyl 3-bromo-4-oxocyclohexane-1-carboxylate

Product 1

HCID 12917745Ethyl 2-methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of EXAMPLE 387A (4.4 g) and ethanethioamide (1.33 g) in N,N-dimethylformamide (50 mL) was heated at 140° C. for 20 hours. After it cooled to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica to give the title compound.

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted with additional ethyl acetate three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-51e7389e38114bae8bc1cf25a7bf8639
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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