Morpholine → 1-Methyl-3-(3-morpholino-1,2-benzisothiazol-5-yl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 1274609Notes

Reaction equation

HRID 1274609 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[C:8]([N:11]3[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]3=[O:23])[CH:9]=[CH:10][C:5]=2[S:4][N:3]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1.CCCCCCC>[CH3:22][N:13]1[C:14]([C:18]([F:21])([F:20])[F:19])=[CH:15][C:16](=[O:17])[N:11]([C:8]2[CH:9]=[CH:10][C:5]3[S:4][N:3]=[C:2]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[C:6]=3[CH:7]=2)[C:12]1=[O:23]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 159065613-(3-chloro-1,2-benzisothiazol-5-yl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 221198881-Methyl-3-(3-morpholino-1,2-benzisothiazol-5-yl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedioneYield 61.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

A mixture of 3-(3-chloro-1,2-benzisothiazol-5-yl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.300 g), morpholine (2.00 g) and triethylamine (5.00 g) in tetrahydrofuran is refluxed for 18 hours and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and 25% and 50% ethyl acetate in heptane solutions gives the title product as a yellow solid (0.210 g, mp 200-205° C.).

Workup

  1. temperatureis refluxed for 18 hours
  2. concentrationconcentrated in vacuo
  3. customto obtain a residue

Sources & evidence

ORD record
ord-c72c8a357b31446a93d95185e8d747a5
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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