Dimethylformamide → 1,1',1''-(1,3,5-Triazine-2,4,6-triyl)tri(pyrrolidin-2-one)

HRID 1872270Notes

Reaction equation

HRID 1872270 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[N:13]=[C:12]([NH:14][C:15](=[O:20])[CH2:16][CH2:17][CH2:18]Cl)[N:11]=[C:10]([NH:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25]Cl)[N:9]=1)=[O:6].CN(C=O)C.CC(C)([O-])C.[K+]>C(Cl)Cl>[N:7]1([C:8]2[N:13]=[C:12]([N:14]3[CH2:18][CH2:17][CH2:16][C:15]3=[O:20])[N:11]=[C:10]([N:21]3[CH2:25][CH2:24][CH2:23][C:22]3=[O:27])[N:9]=2)[CH2:2][CH2:3][CH2:4][C:5]1=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11812220HCID 11812220, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 153465011,1',1''-(1,3,5-Triazine-2,4,6-triyl)tri(pyrrolidin-2-one)Yield 54.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

440 mg of N,N',N"-tris(4-chlorobutyryl)melamine was placed in a flask equipped with a magnetic stirring bar, a reflux condenser, an argon inlet and a rubber septum. To the flask was added 6 ml DMF followed by 450 mg potassium tert-butoxide, while stirring the reaction mixture at room temperature for about 30 minutes. It was then diluted with CH2Cl2 and filtered. The filtrate was concentrated to dryness under reduced pressure. The residue was then purified by column chromatography (silica gel) to give 180 mg of pure 2,4,6-tris(pyrrolidin-2-on-1-yl)-1,3,5-triazine.

Workup

  1. customequipped with a magnetic stirring bar, a reflux condenser, an argon inlet
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. customThe residue was then purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-7cf24ed02bbd4c7299b8f7ea069969b0
Source dataset
uspto-grants-2000_08
Patent number
US06107369

Reaction notes

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