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

HRID 1859195Notes

Reaction equation

HRID 1859195 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 59.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

400 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-bb72acc26ee84c048e19c82f7ee8146f
Source dataset
uspto-grants-2000_11
Patent number
US06153672

Reaction notes

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