Acetal → 1,3,5-Triazine-2,4-diamine, 3,6-dihydro-N2,N2,6-trimethyl-, hydrochloride (1:1)

HRID 874151Notes

Reaction equation

HRID 874151 reaction equation
[CH3:1][N:2]([C:4]([N:6]=[C:7]([NH2:9])[NH2:8])=[NH:5])[CH3:3].[ClH:10].[CH2:11](OC(OCC)C)[CH3:12]>C(O)C(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[ClH:10].[NH2:8][C:7]1[NH:6][C:4]([N:2]([CH3:3])[CH3:1])=[N:5][CH:11]([CH3:12])[N:9]=1

Participants

5

Reactant 2

HCID 7765AcetalHCID 14219Metformin Hydrochloride

Product 1

HCID 101764861,3,5-Triazine-2,4-diamine, 3,6-dihydro-N2,N2,6-trimethyl-, hydrochloride (1:1)Yield 77.6%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6560IsobutanolSolvent

Conditions

Temperature
10 °C

Procedure

Comparative experiment) A mixture of 250.2 g of metformin hydrochloride, 213.6 g of acetaldehyde diethyl acetal and 12.5 g of toluene-4-sulfonic acid monohydrate in 500 ml of isobutanol was heated under reflux for 40 hours. Some of the solvent was removed by distillation. The mixture was cooled to 10° C., and the white precipitate was separated off, giving 224.7 g (77.4%) of 4-amino-3,6-dihydro-2-dimethylamino-6-methyl-1,3,5-triazine hydrochloride.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 40 hours
  3. customSome of the solvent was removed by distillation
  4. customthe white precipitate was separated off

Sources & evidence

ORD record
ord-c879830670284ceba19d166f8c268531
Source dataset
uspto-grants-2015_03
Patent number
US08980828B2

Reaction notes

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