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

HRID 277352

反応式

HRID 277352 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a8fc7eb9a01f44aba5b5a4ad22ee62cb
出典データセット
uspto-grants-2002_03
特許番号
US06355796B1

関連ノート

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