Sodium Bicarbonate → Methyl 5-(6,7-dihydro-4H-pyrano[4,3-d]thiazol-2-yl)-2,4-dimethylbenzoate

HRID 541457Notes

Reaction equation

HRID 541457 reaction equation
[C:1]([C:4]1[C:5]([CH3:15])=[CH:6][C:7]([CH3:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[S:3])[NH2:2].C(=O)(O)[O-].[Na+].Br[CH:22]1[C:27](=O)[CH2:26][CH2:25][O:24][CH2:23]1>C(O)C>[N:2]1[C:27]2[CH2:26][CH2:25][O:24][CH2:23][C:22]=2[S:3][C:1]=1[C:4]1[C:5]([CH3:15])=[CH:6][C:7]([CH3:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 222245413-Bromooxan-4-one2×HCID 86672528Methyl 5-carbamothioyl-2,4-dimethylbenzoate2×

Product 1

HCID 68288977Methyl 5-(6,7-dihydro-4H-pyrano[4,3-d]thiazol-2-yl)-2,4-dimethylbenzoateYield 126.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 5-carbamothioyl-2,4-dimethylbenzoate (compound 130.1, 500 mg, 2.24 mmol, 1.00 equiv) in ethanol (5 mL) was added sodium bicarbonate (396 mg, 4.71 mmol, 1.00 equiv) and 3-bromodihydro-2H-pyran-4(3H)-one (compound 1.10.1, 186 mg, 1.04 mmol, 1.00 equiv). The resulting solution was stiffed overnight at 80° C. under nitrogen. After cooling to room temperature the mixture was concentrated under reduced pressure. The residue was taken up 10 mL of water and ethyl acetate. The aqueous phase was extracted with 2×20 mL of ethyl acetate and the combined organic layers were dried (MgSO4), and concentrated under reduced pressure to yield 400 mg (56%) of the title compound as a yellow solid.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. extractionThe aqueous phase was extracted with 2×20 mL of ethyl acetate
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ee80d953db84c82b602f57a4a7f8867
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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