Dabco → HCID 12760247, compound

HRID 918261Notes

Reaction equation

HRID 918261 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[NH:10][C:11]([O:13][CH3:14])=[O:12].[CH2:15]1[N:20]2[CH2:21][CH2:22][N:17](CC2)C1.[N:23]([CH:26]1[CH2:31][C:30]([CH2:33][N:34]=[C:35]=[O:36])([CH3:32])[CH2:29][C:28]([CH3:38])([CH3:37])[CH2:27]1)=[C:24]=[O:25]>C(Cl)(Cl)Cl>[CH3:14][O:13][C:11]([NH:10][C:2]1[N:3]([C:24]([NH:23][CH:26]2[CH2:31][C:30]([CH2:33][NH:34][C:35]([N:17]3[C:22]4[CH:9]=[CH:4][CH:5]=[CH:6][C:21]=4[N:20]=[C:15]3[NH:10][C:11]([O:13][CH3:14])=[O:12])=[O:36])([CH3:32])[CH2:29][C:28]([CH3:38])([CH3:37])[CH2:27]2)=[O:25])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=1)=[O:12]

Participants

5

Reactant 3

HCID 9237DabcoHCID 25429CarbendazimHCID 169132Isophorone diisocyanate

Product 1

HCID 12760247HCID 12760247, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of methyl 2-benzimidazolecarbamate (19.1 parts) and triethylenediamine (0.1 part) in chloroform (300 parts) was slowly added 5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane (11.1 parts). The reaction mixture was stirred at room temperature overnight, filtered and the solvent removed from the filtrate under reduced pressure. The residue from the filtrate was triturated with hexane and the product methyl 1-{5-[2-(methoxycarbonylamino)-1-benzimidazolylcarbonylamino]-1,3,3-trimethylcyclohexylmethylcarbamoyl}-2- benzimidazolecarbamate (28.5 parts) was collected by filtration. It exhibited a melting point of 82°-83°C.

Workup

  1. filtrationfiltered
  2. customthe solvent removed from the filtrate under reduced pressure
  3. customThe residue from the filtrate was triturated with hexane
  4. filtrationthe product methyl 1-{5-[2-(methoxycarbonylamino)-1-benzimidazolylcarbonylamino]-1,3,3-trimethylcyclohexylmethylcarbamoyl}-2- benzimidazolecarbamate (28.5 parts) was collected by filtration

Sources & evidence

ORD record
ord-7da916654ea34683b0073fced38a20e7
Source dataset
uspto-grants-1976_07
Patent number
US03970668

Reaction notes

Loading…