Dimethylformamide dimethyl acetal → HCID 13039365, compound

HRID 1395439Notes

Reaction equation

HRID 1395439 reaction equation
Cl.[CH2:2]([O:6][NH:7][C:8]([NH:10][C:11](=N)[NH:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:20])=O)[CH2:3][CH2:4][CH3:5].C[O:23][CH:24](OC)[N:25](C)C>CC#N>[CH3:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:20])[C:13]=1[N:12]1[CH:11]=[N:10][C:8]([NH:7][O:6][CH2:2][CH2:3][CH2:4][CH3:5])=[N:25][C:24]1=[O:23]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178454595HCID 178454595, compound

Product 1

HCID 13039365HCID 13039365, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a magnetically stirred suspension of 12.06 g (38 mmol) of 1-N-butoxy-3-(2,6-dimethylphenyl) amidinourea hydrochloride in 25 ml of CH3CN was added 9.11 g (76 mmol) of N,N-dimethyl-formamide dimethyl acetal and another 25ml of CH3CN. All of the solid dissolved after the reaction was stirred for 5 minutes. The reaction solution was refluxed for two hours and allowed to come to ambient temperature, then concentrated in vacuo to yield the desired product as a white solid. This was combined with 200 ml of H2O to an insoluble, thin gummy solid which was transferred to a separatory funnel and extracted with CHCl3 (3×75 ml). The organic layers were combined, washed with H2O (2×75 ml) and saturated aqueous brine (1×75 ml). All aqueous washes were combined and back-extracted with (2×50 ml), dried (Mg2SO4), filtered and concentrated in vacuo to yield 1-(2,6-dimethylphenyl)-4-n-butoxyamino-1,2-dihydro-1,3,5-triazin-2-one, as a white solid containing some liquid. Tlc (3% NH4OH/iPA) shows four spots, one of same Rf as starting material. The product was triturated with iPA to yield a white solid: m.p. 144°-145° C.

Workup

  1. dissolutionAll of the solid dissolved after the reaction
  2. temperatureThe reaction solution was refluxed for two hours
  3. customto come to ambient temperature
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a09674c7f2834f55a17aa95306bcf582
Source dataset
uspto-grants-1980_05
Patent number
US04203985

Reaction notes

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