Formaldehyde → 3,5-Dimethyl-1-(5-(1-(methoxymethyl)-1-methylethyl)-1,2-oxazol-3-yl)hexahydro-1,3,5-triazin-2-one

HRID 2412531Notes

Reaction equation

HRID 2412531 reaction equation
C=O.[CH3:3][NH:4][C:5]([NH:7][C:8]1[CH:12]=[C:11]([C:13]([CH2:16][O:17][CH3:18])([CH3:15])[CH3:14])[O:10][N:9]=1)=[O:6].CN.[CH3:21][N:22]([CH3:25])[CH:23]=O>O>[CH3:3][N:4]1[CH2:23][N:22]([CH3:25])[CH2:21][N:7]([C:8]2[CH:12]=[C:11]([C:13]([CH2:16][O:17][CH3:18])([CH3:14])[CH3:15])[O:10][N:9]=2)[C:5]1=[O:6]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6228DimethylformamideHCID 6329MethylamineHCID 133396151-Methyl-3-(5-(1-(methoxymethyl)-1-methylethyl)-1,2-oxazol-3-yl)urea

Product 1

HCID 133704613,5-Dimethyl-1-(5-(1-(methoxymethyl)-1-methylethyl)-1,2-oxazol-3-yl)hexahydro-1,3,5-triazin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

16 ml of a 36% aqueous formaldehyde solution was added dropwise to a stirred solution of 4.1 g of 2D in 75 ml of dimethylformamide. The temperature of the mixture rose from 22° C. to 27° C. The mixture was stirred for 30 minutes, then 8 ml of a 40% solution of methylamine in water was added, drop-by-drop. The temperature of the mixture rose from 27° C. to 36° C. The mixture was refluxed for 3 hours, then the solvent was evaporated under reduced pressure. The residue was mixed with cold water, and the resulting mixture was extracted with ether. The solvent was evaporated from the extract, and the residue was crystallized when hexane was added, to give 2, as a white solid, m.p.: 49°-50° C.

Workup

  1. customrose from 22° C. to 27° C
  2. customrose from 27° C. to 36° C
  3. temperatureThe mixture was refluxed for 3 hours
  4. customthe solvent was evaporated under reduced pressure
  5. additionThe residue was mixed with cold water
  6. extractionthe resulting mixture was extracted with ether
  7. customThe solvent was evaporated from the extract
  8. customthe residue was crystallized when hexane
  9. additionwas added
  10. customto give 2

Sources & evidence

ORD record
ord-8a9fe31a776a48e1a9b58fce2cfce625
Source dataset
uspto-grants-1985_01
Patent number
US04493728

Reaction notes

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