N-(hydroxymethyl)phthalimide → Phthalamide

HRID 843708

Reaction equation

HRID 843708 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

HCID 6956PhthalamideYield 168.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b24de7fa85a843819bcf06fc5284d1fb
Source dataset
uspto-grants-2002_04
Patent number
US06380189B1

Linked notes

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