Nitrogen → 2-Bromo-5-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

HRID 1044753

반응식

HRID 1044753 반응식
N#N.[Br:3][C:4]1[S:5][C:6]([C:9](=[O:11])[CH3:10])=[CH:7][N:8]=1.COC([O:17][CH3:18])OC.[C:19]([O-])(O)=O.[Na+]>C(O)CO>[Br:3][C:4]1[S:5][C:6]([C:9]2([CH3:10])[O:17][CH2:18][CH2:19][O:11]2)=[CH:7][N:8]=1

참가 물질

6

반응물 4

HCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 575628131-(2-Bromo-1,3-thiazol-5-yl)ethan-1-one

생성물 1

HCID 668200782-Bromo-5-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

시약·촉매·용매 1

HCID 174Ethylene Glycol용매

반응 조건

온도
95 °C

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a condenser under inert atmosphere (N2), a solution of 1-(2-bromo-thiazol-5-yl)-ethanone (16.22 g, 78.71 mmol) in ethylene glycol (85 mL) was treated with trimethylorthoformate (18 mL, 164.19 mmol) followed by LiBF4 (1.51 g, 15.74 mmol). The reaction mixture was heated at 95° C. for 2 days. Sat. aq. NaHCO3 was added and the mixture was extracted with Et2O (3×). The org. extracts were washed with brine, dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 to 3:1 hept-EA) gave the title compound as a yellow solid. TLC:rf (1:1 hept-EA)=0.63. LC-MS-conditions 02: tR=0.89 min; [M+H]+=250.24.

후처리

  1. extractionthe mixture was extracted with Et2O (3×)
  2. washextracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (20:1 to 3:1 hept-EA)

출처 및 근거

ORD 기록
ord-310be4375919419b9130be1b8e51e298
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563714B2

연결된 노트

불러오는 중…