Sodium Bicarbonate → 6-Dimethylaminomethyl-7-hydroxy-2,3-dimethyl-3H-benzimidazole-5-carboxylic Acid Dimethylamide

HRID 969511Notes

Reaction equation

HRID 969511 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[CH:15]=[C:14]([OH:16])[C:8]2[N:9]=[C:10]([CH3:13])[N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4].[CH3:18][N+:19]([CH3:21])=[CH2:20].[I-].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:17][N:2]([CH3:1])[C:3]([C:5]1[C:15]([CH2:18][N:19]([CH3:21])[CH3:20])=[C:14]([OH:16])[C:8]2[N:9]=[C:10]([CH3:13])[N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724133Dimethyl(methylene)ammounium iodideHCID 534710164-Hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

Product 1

HCID 462226926-Dimethylaminomethyl-7-hydroxy-2,3-dimethyl-3H-benzimidazole-5-carboxylic Acid DimethylamideYield 800.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2.0 g (8.6 mmol) 7-Hydroxy-2,3-dimethyl-3H-benzimidazole-5-carboxylic acid dimethylamide in dichloromethane (80 ml) was added dropwise a suspension of 1.7 g (9.4 mmol) Eschenmoser's salt in dichloromethane (50 ml). After stirring for 3 h at room temperature, the reaction mixture was poured into saturated sodium bicarbonate solution (100 ml) and extracted with dichloromethane (2×50 ml). The organic layers were dried over magnesium sulphate and concentrated in vacuo to give 20 g (82%) of the title compound as an orange foam. The compound was used for the next step without further purification.

Workup

  1. additionwas added dropwise
  2. extractionextracted with dichloromethane (2×50 ml)
  3. dry with materialThe organic layers were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-668a69228e5b4bc0aa36729b839ebb97
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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