N,N-dimethylformamide N,N-dimethylacetamide → 1,3,5-Triazin-2(1H)-one, 1-(2,6-dimethylphenyl)-4-(methylamino)-

HRID 2049543

Reaction equation

HRID 2049543 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH:10][C:11]([NH:13][C:14](=[NH:17])[NH:15][CH3:16])=[O:12].[CH3:18]N(C=O)C.CC(N(C)C)=O>C(#N)C>[CH3:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH3:2])[C:4]=1[N:10]1[CH:16]=[N:15][C:14]([NH:17][CH3:18])=[N:13][C:11]1=[O:12]

Participants

4

Reactant 2

HCID 22628260N,N-dimethylformamide N,N-dimethylacetamideHCID 178485165HCID 178485165, compound

Product 1

HCID 1008051,3,5-Triazin-2(1H)-one, 1-(2,6-dimethylphenyl)-4-(methylamino)-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
105 °C

Procedure

About 200 mg of 1-(2,6-dimethylphenyl)-3-methylamidinourea hydrochloride was introduced in a gas chromatograph hypo vial and dissolved in 1 ml of acetonitrile. To the solution was added 0.2 ml of DMF DMA reagent. The vial was sealed with crimper and heated at 105° C. for 15 minutes in an oven. Seven vials were made. The contents of the vials were then put into a long-neck round bottom flask and evaporated to dryness by a flask evaporator. The solid mass was dissolved in a mixture of 30 ml of CHCl3 and 20 ml of water and shaken vigorously in a 60 ml separatory funnel. The aqueous layer was discarded and 20 ml of water was added and shaken. The CHCl3 layer was then taken and about 10 g of anhydrous Na2SO4 was added, the CHCl3 solution was decanted into a flask and evaporated to dryness. The solid material was dissolved in 2-pentanone (about 80 ml) at 70° C. The solution was concentrated and crystallized upon cooling. The crystals were collected and dried in a desiccator with P2O5 with vacuum for one hour.

Workup

  1. customThe vial was sealed with crimper
  2. customThe contents of the vials were then put into a long-neck round bottom flask
  3. customevaporated to dryness by a flask
  4. customevaporator
  5. dissolutionThe solid mass was dissolved in a mixture of 30 ml of CHCl3 and 20 ml of water
  6. addition20 ml of water was added
  7. stirringshaken
  8. additionabout 10 g of anhydrous Na2SO4 was added
  9. customthe CHCl3 solution was decanted into a flask
  10. customevaporated to dryness
  11. dissolutionThe solid material was dissolved in 2-pentanone (about 80 ml) at 70° C
  12. concentrationThe solution was concentrated
  13. customcrystallized
  14. temperatureupon cooling
  15. customThe crystals were collected
  16. dry with materialdried in a desiccator with P2O5 with vacuum for one hour

Sources & evidence

ORD record
ord-9f19192322fb4c53b8c5638be5daf5db
Source dataset
uspto-grants-1980_04
Patent number
US04198409

Linked notes

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