Water → HCID 11955792, compound

HRID 1789777Notes

Reaction equation

HRID 1789777 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.[H-].[Na+].Cl[C:14]1[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:17]=[C:16]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[N:15]=1.O>CN(C=O)C>[NH2:1][C:2]1[N:6]([C:14]2[N:19]=[C:18]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[N:17]=[C:16]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[N:15]=2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 136242-AminobenzimidazoleHCID 24758Sodium hydrideHCID 2249672-Chloro-4,6-bis(morpholin-4-yl)-1,3,5-triazine

Product 1

HCID 11955792HCID 11955792, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

9.32 g (70 mmol) of 2-aminobenzimidazole dissolved in DMF (300 ml) was added and reacted with 60% sodium hydride (2.80 g, 70 mmol) at room temperature for 30 minutes. This suspension was added to a solution of 14.3 g (50 mmol) of 2-chloro-4,6-dimorpholino-1,3,5-triazine dissolved in DMF (200 ml) and stirred at room temperature for 2 hours. The reaction solution was poured into water and the resulting precipitates were washed with water and methanol to obtain 17.7 g (yield: 93%) of 2-(2-aminobenz-imidazol-1-yl)-4,6-dimorpholino-1,3,5-triazine. (2) 0.38 g (1.0 mmol) of 2-(2-aminobenzimidazol-1-yl)-4,6-dimorpholino-1,3,5-triazine and 0.24 g (4.0 mmol) of acetic acid were added to and further 0.83 g (4.0 mmol) of DCC was added to chloroform (5 ml) and stirred at room temperature for 4 hours. The reaction solution was poured into water and extracted with ethyl acetate. The separated organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography to obtain 0.31 g (yield: 73%) of the titled compound as colorless crystals.

Workup

  1. additionwas added
  2. customthe resulting precipitates
  3. washwere washed with water and methanol

Sources & evidence

ORD record
ord-ea4fa84f58b14006b5a9e9d83c326429
Source dataset
uspto-grants-2006_07
Patent number
US07071189B2

Reaction notes

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