N-(hydroxymethyl)phthalimide → Phthalamide

HRID 843708

反応式

HRID 843708 の反応式
CC1C2C(=O)OC(=O)[NH:11]C=2C=CC=1.OC[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]>CS(O)(=O)=O.CCOCC>[C:17]([NH2:11])(=[O:26])[C:18]1[C:19](=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:20]([NH2:16])=[O:21]

参加物

5

反応物 2

HCID 8354N-(hydroxymethyl)phthalimideHCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

生成物 1

HCID 6956Phthalamide収率 168.5%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6395Methanesulfonic Acid溶媒

反応条件

温度
50 °C

実験手順

To a solution of 5-methyl-4H-3,1-benzoxazin-2,4-dione (Preparation VIIA) (19.7 g, 111 mmol) in methanesulfonic acid (150 mL) was added N-(hydroxymethyl)phthalimide (20.3 g, 111 mmol). The reaction mixture was heated to 50° C. and stirred for 3 hours. After cooling to room temperature, the reaction mixture was diluted with 2000 mL of Et2O. After stirring for an additional 1 hour, the precipitate was filtered, washed with Et2O and dried affording 30.7 g of crude phthalamide. 1H NMR showed a 3:2 mixture of the 6- and 8-substituted regioisomers respectively. The crude material was used directly in the next reaction where the two regeoisomers were separated.

後処理

  1. temperatureAfter cooling to room temperature
  2. stirringAfter stirring for an additional 1 hour
  3. filtrationthe precipitate was filtered
  4. washwashed with Et2O
  5. customdried

出典と根拠

ORDレコード
ord-b24de7fa85a843819bcf06fc5284d1fb
出典データセット
uspto-grants-2002_04
特許番号
US06380189B1

関連ノート

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