4-Methylmorpholine → HCID 14990285, compound

HRID 1645746Notes

Reaction equation

HRID 1645746 reaction equation
CN1CCOCC1.CN(C1C=CC=CN=1)C.[C:17]([NH:21][C:22]([C:24]1[S:28][N:27]=[C:26]([CH:29]([CH3:31])[CH3:30])[C:25]=1[C:32]([OH:34])=O)=[O:23])([CH3:20])([CH3:19])[CH3:18]>ClCCl>[C:17]([N:21]1[C:22](=[O:23])[C:24]2[S:28][N:27]=[C:26]([CH:29]([CH3:31])[CH3:30])[C:25]=2[C:32]1=[O:34])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 218852-DimethylaminopyridineHCID 14990284HCID 14990284, compound

Product 1

HCID 14990285HCID 14990285, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7.5 g (74.1 mmol) of methylmorpholine, 2.4 g (20 mmol) of dimethylaminopyridine and 17.4 g of a 50% strength solution of propanephosphonic anhydride (27.3 mmol) in dichloromethane were added dropwise in succession to 5.4 g (20 mmol) of 5-tert-butylaminocarbonyl-3-isopropylisothiazole-4-carboxylic acid in 200 ml of dichloromethane at -5° C. and the mixture was then refluxed for 6 hours. Working up was carried out as described above for Example No. 1.003. 4.8 g (95%) of N-tert-butyl-3-isopropylisothiazole-4,5-dicarboximide were obtained as a solid of melting point 52°-53° C. (Example No. 3.001).

Workup

  1. temperaturethe mixture was then refluxed for 6 hours

Sources & evidence

ORD record
ord-58cc67267e8f41b29f83b0041973e9bf
Source dataset
uspto-grants-1993_01
Patent number
US05176739

Reaction notes

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