2-Bromocyclohexanone → Methyl 3-(4,5,6,7-tetrahydrobenzothiazol-2-ylmethoxy)benzoate

HRID 1602491Notes

Reaction equation

HRID 1602491 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[C:9]([CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18])(=[S:11])[NH2:10]>O1CCOCC1>[S:11]1[C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:2]=2[N:10]=[C:9]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 117897582-BromocyclohexanoneHCID 19611422Methyl 3-thiocarbamoylmethoxybenzoate

Product 1

HCID 19611521Methyl 3-(4,5,6,7-tetrahydrobenzothiazol-2-ylmethoxy)benzoateYield 27.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

After a mixture of 2-bromocyclohexanone (865 mg, 4.9 mmol), methyl 3-(thiocarbamoylmethoxy)benzoate (1.00 g, 4.4 mmol) and 1,4-dioxane (10 ml) was stirred at room temperature for 5 hours and then at 80° C. for 12 hours, it was cooled and concentrated under reduced pressure. Saturated sodium bicarbonate aqueous solution was added to the resulting residue and the product formed was extracted with ethyl acetate. The extract was washed with water and brine in that order, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (eluent=hexane:ethyl acetate=4:1) to give methyl 3-(4,5,6,7-tetrahydrobenzothiazol-2-ylmethoxy)benzoate (369 mg, 1.2 mmol, 27%).

Workup

  1. waitat 80° C. for 12 hours
  2. temperatureit was cooled
  3. concentrationconcentrated under reduced pressure
  4. additionSaturated sodium bicarbonate aqueous solution was added to the resulting residue
  5. customthe product formed
  6. extractionwas extracted with ethyl acetate
  7. washThe extract was washed with water and brine in that order
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThereafter, the resulting residue was purified by silica gel column chromatography (eluent=hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-90d3decdfeb643aebe6f0ba671ed51e1
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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