Acetone → 1,3,5-Triazino(1,2-a)benzimidazol-4(1H)-one, 2,3-dihydro-2,2-dimethyl-

HRID 615081Notes

Reaction equation

HRID 615081 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Cl[NH:12][CH:13]=[O:14].[CH3:15][C:16]([CH3:18])=O>>[CH3:15][C:16]1([CH3:18])[NH:12][C:13](=[O:14])[N:6]2[C:2](=[N:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=32)[NH:1]1

Participants

4

Reactant 3

HCID 180Acetone3×HCID 136242-AminobenzimidazoleHCID 12663091N-Chloroformamide

Product 1

HCID 1355690331,3,5-Triazino(1,2-a)benzimidazol-4(1H)-one, 2,3-dihydro-2,2-dimethyl-

Procedure

A mixture of 16 g (0.12 mole) of 2-aminobenzimidazole, 100 ml of acetone and 16 g of 3A molecular sieves was stirred and heated under reflux, adding 8 g of additional sieves after 24 hours. Refluxing was continued for a total period of 3 days, after which the mixture was allowed to cool and a solution of 4.77 g (0.06 mole) of N-chloroformamide(1) in ~25 ml. of acetone added dropwise with stirring. The mixture was warmed to the reflux point several times and the rate of N-chloroformamide addition adjusted to keep the temperature just below the reflux point. An additional 50 ml of acetone were added to facilitate stirring of the thickening reaction mixture. Upon completion of the feed, the reaction flask was fitted with a drying tube and the mixture stirred for 3 days at room temperature. The reaction mixture was then evaporated under reduced pressure to give 9.3 g of a tan solid. The latter was extracted with boiling acetone to separate an insoluble fraction and the acetone solution evaporated to give the crude solid product. The latter material was chromatographed on silica, eluting with CHCl3 /CH3OH (80:5). Fractions 3 through 8 were combined and evaporated to give 3.9 g of product, mp 178°-180° C. (dec).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. additionadding 8 g of additional sieves after 24 hours
  4. temperatureRefluxing
  5. temperatureto cool
  6. stirringwith stirring
  7. temperatureThe mixture was warmed to the reflux point several times
  8. stirringto facilitate stirring of the thickening reaction mixture
  9. customUpon completion of the feed, the reaction flask was fitted with a drying tube
  10. stirringthe mixture stirred for 3 days at room temperature
  11. customThe reaction mixture was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-ac2dde96048c4d0d8eccaa431eedb5ca
Source dataset
uspto-grants-1985_02
Patent number
US04497650

Reaction notes

Loading…