Phosphorus pentachloride → 2-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-one

HRID 277352

반응식

HRID 277352 반응식
[CH3:1][N:2]([CH3:17])[C:3]([NH:5]/[C:6](/[C:13]([F:16])([F:15])[F:14])=[CH:7]\[C:8]([O:10]CC)=[O:9])=O.P(Cl)(Cl)(Cl)(Cl)Cl>O=P(Cl)(Cl)Cl>[CH3:17][N:2]([CH3:1])[C:3]1[O:10][C:8](=[O:9])[CH:7]=[C:6]([C:13]([F:14])([F:15])[F:16])[N:5]=1

참가 물질

4

반응물 2

HCID 24819Phosphorus pentachlorideHCID 11334267Ethyl (Z)-3-(dimethylcarbamoylamino)-4,4,4-trifluoro-but-2-enoate

생성물 1

HCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-one수율 93.8%

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

실험 절차

A solution of ethyl 3-[N-(N,N-dimethylcarbamoyl)-amino]-4,4,4-trifluorocrotonate (5.08 g, 0.02 mol) in phosphorus oxytrichloride (3 mL) is treated with phosphorus pentachloride (4.16 g, 0.02 mol) in three portions at 15 minute intervals, stirred for 30 minutes, and quenched with ice and water. The resultant aqueous mixture is extracted with ethyl acetate. The organic layer is washed sequentially with saturated sodium bicarbonate and water, and evaporated to give the title product as a white solid (3.9 g, 93.8% yield) which is identical by 1H and 19F NMR to a sample prepared by the literature procedure (Bull. Soc. Chem. Belg. 101, 313, 1992). The title product is further purified by crystallization from heptane (74.5% crystallized yield).

후처리

  1. customquenched with ice and water
  2. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  3. washThe organic layer is washed sequentially with saturated sodium bicarbonate and water
  4. customevaporated

출처 및 근거

ORD 기록
ord-a8fc7eb9a01f44aba5b5a4ad22ee62cb
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355796B1

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