Acetic Acid → N2-Mesityl-1-methyl-N7,N7-dipropyl-1H-benzimidazole-2,7-diamine

HRID 2235534Notes

Reaction equation

HRID 2235534 reaction equation
[C:1]1([CH3:21])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]([NH2:20])=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]=1.[CH:22](=O)[CH2:23][CH3:24].[BH3-][C:27]#N.[Na+].[C:30](O)(=O)[CH3:31]>CO.C(OCC)(=O)C>[C:1]1([CH3:21])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]([N:20]([CH2:27][CH2:30][CH3:31])[CH2:22][CH2:23][CH3:24])=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 86049130N2-Mesityl-1-methyl-1H-benzimidazole-2,7-diamine

Product 1

HCID 11210737N2-Mesityl-1-methyl-N7,N7-dipropyl-1H-benzimidazole-2,7-diamineYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing 0.05 g (0.18 mmol) of N2-mesityl-1-methyl-1H-benzimidazole-2,7-diamine in methanol (5 ml) was added 0.03 ml (0.54 mmol) of propionaldehyde, 0.03 g (0.54 mmol) of NaBH3CN and 0.1 ml of acetic acid. The mixture was stirred overnight then diluted with ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via Biotage chromatography eluting with 5% methanol/dichloromethane gave 0.04 g (70%) of product.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationFiltration, removal of solvent and purification of the residue via Biotage chromatography
  4. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-42bcf7ca17e5409bb08b00eaea192bcf
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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