N-(hydroxymethyl)phthalimide → Phthalamide

HRID 843708

반응식

HRID 843708 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

HCID 6956Phthalamide수율 168.5%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6395Methanesulfonic Acid용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b24de7fa85a843819bcf06fc5284d1fb
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380189B1

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