Water → HCID 69135108, compound

HRID 969534Notes

Reaction equation

HRID 969534 reaction equation
C([O:8][C:9]1[C:14]2[N:15]=[C:16]([CH3:19])[N:17]([CH3:18])[C:13]=2[CH:12]=[C:11]([N:20]([CH3:24])[C:21](=[O:23])[CH3:22])[CH:10]=1)C1C=CC=CC=1.[I-].O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:16][N:17]([CH2:18][C:10]1[C:11]([N:20]([CH3:24])[C:21](=[O:23])[CH3:22])=[CH:12][C:13]2[N:17]([CH3:18])[C:16]([CH3:19])=[N:15][C:14]=2[C:9]=1[OH:8])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 30165Iodide IonHCID 516892Sodium BicarbonateHCID 69135068HCID 69135068, compound

Product 1

HCID 69135108HCID 69135108, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4.7 g (18.9 mmol) N-(7-benzyloxy-2,3-dimethy-3H-benzimidazol-5-yl)-N-methyl-acetamide in dry dichloromethane (200 ml) was treated with 4.5 g (24.6 mmol) N,N-dimethylmethylenimmonium iodide and the reaction was stirred overnight at room temperature. The reaction mixture was poured into water, neutralized with sat. sodium bicarbonate solution and extracted with dichloromethane (2×20 ml). The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue afforded 2.2 g (41%) of the title compound as a white solid. m.p. 181°-184° C.

Workup

  1. extractionextracted with dichloromethane (2×20 ml)
  2. dry with materialThe organic layers were dried over magnesium sulphate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ab463a49a5e41eb89c6847f57acef93
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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