Acetyl chloride → 1,3,5-Triazino(1,2-a)benzimidazol-4(3H)-one, 10-acetyl-2,10-dihydro-2,2,3-trimethyl-

HRID 615090Notes

Reaction equation

HRID 615090 reaction equation
[CH3:1][C:2]1([CH3:17])[N:10]([CH3:11])[C:9](=[O:12])[N:8]2[C:4](=[N:5][C:6]3[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=32)[NH:3]1.[C:18](Cl)(=[O:20])[CH3:19].Cl.C([NH+](CC)CC)C.[NH4+].[OH-]>CO.C(Cl)(Cl)Cl.C(N(CC)CC)C.CC(C)=O>[C:18]([N:5]1[C:6]2[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=2[N:8]2[C:9](=[O:12])[N:10]([CH3:11])[C:2]([CH3:17])([CH3:1])[N:3]=[C:4]12)(=[O:20])[CH3:19]

Participants

9

Reactant 4

HCID 6367Acetyl chlorideHCID 14923Ammonium HydroxideHCID 1591201,2-dihydro-2,2,3-trimethyl-1,3,5-triazino[1,2-a]benzimidazol-4(3H)-oneHCID 21900368Triethylammonium hydrochloride

Product 1

HCID 1591101,3,5-Triazino(1,2-a)benzimidazol-4(3H)-one, 10-acetyl-2,10-dihydro-2,2,3-trimethyl-Yield 52%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

A 250-ml, round-bottomed flask containing a magnetic stirring bar was charged with 2.45 g (0.0106 mole) of 1,2-dihydro-2,2,3-trimethyl-1,3,5-triazino[1,2-a]benzimidazol-4-(3H)-one, 150 ml of acetone and 1.53 ml of triethylamine. Acetyl chloride (0.86 g, 0.0110 mole) was added rapidly via syringe to the resulting solution. The mixture was stirred for two hours at room temperature after which time a white precipitate of triethylammonium hydrochloride was visible. Examination of the reaction mixture by TLC (silica, 80:2:1, CHCl3 : CH3OH: NH4OH) showed that only a trace of starting material remained. The mixture was concentrated in vacuo and the resulting solid was taken up in methylene chloride. The resulting solution was washed with water (3 times) brine, dried (MgSO4) and concentrated under reduced pressure to afford 1.5 g (52% yield) of a white solid which was analytically pure, mp 159°-62° C.

Workup

  1. additionA 250-ml, round-bottomed flask containing a magnetic stirring bar
  2. concentrationThe mixture was concentrated in vacuo
  3. washThe resulting solution was washed with water (3 times) brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f022793528184ecaaac2705f4a4ba12d
Source dataset
uspto-grants-1985_02
Patent number
US04497650

Reaction notes

Loading…