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

HRID 541457노트

반응식

HRID 541457 반응식
[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]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 222245413-Bromooxan-4-one2회HCID 86672528Methyl 5-carbamothioyl-2,4-dimethylbenzoate2회

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ee80d953db84c82b602f57a4a7f8867
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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