Dimethylformamide → HCID 15045486, compound

HRID 1090645Notes

Reaction equation

HRID 1090645 reaction equation
C[N+](C)=CCl.[Cl-].P(Cl)(Cl)(Cl)=O.[CH2:12]([N:15]1[C:24](=[O:25])[CH:23]=[C:18]2[S:19][CH2:20][CH2:21][CH2:22][N:17]2[C:16]1=[O:26])[CH2:13][CH3:14].CN([CH:30]=[O:31])C>>[CH:30]([C:23]1[C:24](=[O:25])[N:15]([CH2:12][CH2:13][CH3:14])[C:16](=[O:26])[N:17]2[CH2:22][CH2:21][CH2:20][S:19][C:18]=12)=[O:31]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 15027560HCID 15027560, compound

Product 1

HCID 15045486HCID 15045486, compoundYield 95%

Procedure

The Vilsmeier reagent prepared from phosphorus oxychloride (3.7 ml) and DMF (6.2 ml) was added dropwise to a solution of 7-propyl-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione (6 g) in DMF (38 ml) with stirring under ice cooling. The reaction solution was stirred at room temperature for 3 hours and then, poured on ice water. The mixture was stirred for a while and the precipitated crystals were recrystallized from ethyl acetate to give colorless crystals (6.46 g, 95%).

Workup

  1. stirringThe reaction solution was stirred at room temperature for 3 hours
  2. additionpoured on ice water
  3. stirringThe mixture was stirred for a while
  4. customthe precipitated crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e9bb57c254124a7e906f2dbc17ebe420
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

Loading…