Pyridine → 8-Methyl-2-[2-methyl-6-(trifluoromethyl)-3-pyridinyl]-4H-3,1-benzoxazine

HRID 352454노트

반응식

HRID 352454 반응식
C[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[NH:12][C:11](=O)[O:10][C:8](=O)[C:7]=12.[CH3:14][C:15]1[C:20](C(Cl)=O)=[CH:19][CH:18]=[C:17]([C:24]([F:27])([F:26])[F:25])[N:16]=1.N1C=CC=C[CH:29]=1>>[CH3:29][C:5]1[C:6]2[N:12]=[C:11]([C:20]3[C:15]([CH3:14])=[N:16][C:17]([C:24]([F:27])([F:25])[F:26])=[CH:18][CH:19]=3)[O:10][CH2:8][C:7]=2[CH:2]=[CH:3][CH:4]=1

참가 물질

4

반응물 3

HCID 1049PyridineHCID 27756752-Methyl-6-(trifluoromethyl)nicotinoyl chlorideHCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

생성물 1

HCID 222503278-Methyl-2-[2-methyl-6-(trifluoromethyl)-3-pyridinyl]-4H-3,1-benzoxazine

실험 절차

A mixture of the 6-methyl isatoic anhydride (3.92 g, 22.1 mmol) and the acid chloride from Step A (5.45 g, 24.3 mmol) was heated at reflux in pyridine for 16 hours. The dark brown solution was cooled to room temperature and the solvent was removed under reduced pressure. Excess pyridine was removed by azeotrope with toluene. Ether was added and the resulting brown solid was removed by filtration. The solid was taken up in a mixture of aqueous sodium bicarbonate and chloroform, the chloroform extracts were dried over magnesium sulfate and evaporated. Excess pyridine was again removed by azeotrope with toluene to afford 5.1 g of the title compound as a brown solid.

후처리

  1. customthe solvent was removed under reduced pressure
  2. customExcess pyridine was removed by azeotrope with toluene
  3. additionEther was added
  4. customthe resulting brown solid was removed by filtration
  5. additionThe solid was taken up in a mixture of aqueous sodium bicarbonate and chloroform
  6. dry with materialthe chloroform extracts were dried over magnesium sulfate
  7. customevaporated
  8. customExcess pyridine was again removed by azeotrope with toluene

출처 및 근거

ORD 기록
ord-05fc5cebd6b04ad8846426bd2114d799
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747047B2

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