N-Methylaniline → HCID 19819742, compound

HRID 1031181Notes

Reaction equation

HRID 1031181 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:10][CH2:11][CH:12]1[N:25]([CH3:26])[C:17]2=[N:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:16]2[C:15](=[O:27])[N:14]([CH3:28])[CH2:13]1>>[CH3:26][N:25]1[C:17]2=[N:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:16]2[C:15](=[O:27])[N:14]([CH3:28])[CH2:13][CH:12]1[CH2:11][CH2:10][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 7515N-MethylanilineHCID 198197592-(2-Chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one

Product 1

HCID 19819742HCID 19819742, compound

Conditions

Temperature
60 °C

Procedure

To 15 mL of N-methylaniline was added 3.0 g (0.01 mol) of 2-(2-chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one. The reaction was heated at 60° C. for 1.5 hr, then 100° C. for ~48 hr. The N-methylaniline was removed by distillation. The residue was dissolved in 100 mL of CH2Cl2, washed with 2×100 mL of 1N NaOH and dried over Na2SO4. The organic phase was filtered and concentrated by rotary evaporation. The residue was then heated to 100° C., 0.5 mm Hg to remove any residual starting amine. The crude syrup was crystallized from toluene/iso-octane to afford 2.0 g (55%) of white analytically pure crystals, mp 74°-90° C.

Workup

  1. wait100° C. for ~48 hr
  2. customThe N-methylaniline was removed by distillation
  3. dissolutionThe residue was dissolved in 100 mL of CH2Cl2
  4. washwashed with 2×100 mL of 1N NaOH
  5. dry with materialdried over Na2SO4
  6. filtrationThe organic phase was filtered
  7. concentrationconcentrated by rotary evaporation
  8. temperatureThe residue was then heated to 100° C.
  9. custom0.5 mm Hg to remove
  10. customThe crude syrup was crystallized from toluene/iso-octane
  11. customto afford 2.0 g (55%) of white analytically pure crystals, mp 74°-90° C.

Sources & evidence

ORD record
ord-3520ffbeef724717addc10044a72e1d4
Source dataset
uspto-grants-1992_04
Patent number
US05109013

Reaction notes

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