4-Methylmorpholine → N-tert-butyl-5-methylisoxazole-3,4-dicarboximide

HRID 1645747Notes

Reaction equation

HRID 1645747 reaction equation
CN1CCOCC1.CN(C1C=CC=CN=1)C.[C:17]([NH:21][C:22]([C:24]1[C:28]([C:29](O)=[O:30])=[C:27]([CH3:32])[O:26][N:25]=1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>ClCCl>[C:17]([N:21]1[C:29](=[O:30])[C:28]2[C:24](=[N:25][O:26][C:27]=2[CH3:32])[C:22]1=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 218852-DimethylaminopyridineHCID 10513407HCID 10513407, compound

Product 1

HCID 14990286N-tert-butyl-5-methylisoxazole-3,4-dicarboximideYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6.3 g (62.2 mmol) of methylmorpholine, 2.4 g (20 mmol) of dimethylaminopyridine and 14.6 g of a 50% strength solution of propanephosphonic anhydride (23 mmol) in dichloromethane were added dropwise in succession to 3.8 g (16.8 mmol) of 3-tert-butylaminocarbonyl-5-methylisoxazole-4-carboxylic acid in 150 ml of dichloromethane at -5° C. and the mixture was then refluxed for 6 hours. Working up was carried out as described above. 3.2 g (91%) of N-tert-butyl-5-methylisoxazole-3,4,-dicarboximide were obtained as a solid of melting point 48°-50° C. (Example No. 2.001).

Workup

  1. temperaturethe mixture was then refluxed for 6 hours

Sources & evidence

ORD record
ord-8ecba8a761d7499d81c3f5ab68699623
Source dataset
uspto-grants-1993_01
Patent number
US05176739

Reaction notes

Loading…