Cyromazine → HCID 20147132, compound

HRID 569470

Reaction equation

HRID 569470 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].[NH2:9][C:10]1[N:15]=[C:14]([NH2:16])[N:13]=[C:12]([NH:17][CH:18]2[CH2:20][CH2:19]2)[N:11]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH:18]1([NH:17][C:12]2[N:11]=[C:10]([NH:9][C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3])[N:15]=[C:14]([NH:16][C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3])[N:13]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 47866CyromazineHCID 62365Isobutyl chloroformate

Product 1

HCID 20147132HCID 20147132, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

16.4 g (0.12 mol) of isobutyl chloroformate are added dropwise to a mixture of 8.3 g (0.05 mol) of 2,4-diamino-6-cyclopropylamino-s-triazine, 0.5 g of 4-dimethylaminopyridine and 125 ml of pyridine. The batch is stirred for 1 hour at room temperature and then for 1 hour at 55°-60° C. After the precipitate has been filtered off, the reaction mixture is concentrated by evaporation in a water-jet vacuum, the residue is taken up in 150 ml of chloroform and extracted with 100 ml of water. After drying over sodium sulfate, the solvent is distilled off, and the crude product is purified by column chromatography through silica with methylene chloride as eluant.

Workup

  1. waitfor 1 hour at 55°-60° C
  2. filtrationAfter the precipitate has been filtered off
  3. concentrationthe reaction mixture is concentrated by evaporation in a water-jet vacuum
  4. extractionextracted with 100 ml of water
  5. dry with materialAfter drying over sodium sulfate
  6. distillationthe solvent is distilled off
  7. customthe crude product is purified by column chromatography through silica with methylene chloride as eluant

Sources & evidence

ORD record
ord-7b155abe100d4b31855dc61131fa66b2
Source dataset
uspto-grants-1988_03
Patent number
US04732899

Linked notes

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