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

HRID 2040335Notes

Reaction equation

HRID 2040335 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-349f54bfa70f422d8f79814062b9a8bd
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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