Dimethylformamide → HCID 697349, compound

HRID 2353045Notes

Reaction equation

HRID 2353045 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:15]=[CH:14]C2N[C:11](=O)[NH:12][C:8]=2[CH:7]=1)([O-:5])=[O:4].[CH3:16][N:17]([CH:19]=[O:20])[CH3:18]>>[CH3:16][N:17]1[C:18]2[CH:14]=[CH:15][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][C:8]=2[N:12]([CH3:11])[C:19]1=[O:20]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 37256112H-Benzimidazol-2-one, 1,3-dihydro-5-nitro-

Product 1

HCID 697349HCID 697349, compoundYield 93%

Procedure

DMF (10 ml) was added to 0.6 g of 60% NaH (15.12 mM) in a 100 mL round bottom flask under N2. Added to the flask was 1.29 g of 5-nitro-2-benzimidazolinone (7.20 mM) in 10 mL DMF and rinsed with 10 mL more DMF. The solution was stirred 25 minutes and 10.22 g MeI (72 mM) was added and then stirred a further 3 hours. HCl (200 mL, 1 M) was added to the solution and then was extracted with EtOAc, washed with brine, and dried over MgSO4 and then concentrated in vacuo and flashed 0 to 100% EtOAc in hexanes to give 1.4 g of 1,3-dimethyl-5-nitro-1H-benzo[d]imidazol-2(3H)-one (93% yield).

Workup

  1. additionAdded to the flask
  2. washrinsed with 10 mL more DMF
  3. addition10.22 g MeI (72 mM) was added
  4. stirringstirred a further 3 hours
  5. additionHCl (200 mL, 1 M) was added to the solution
  6. extractionwas extracted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84281830b1cf49c8aa3225c5accfe3e5
Source dataset
uspto-grants-2010_07
Patent number
US07749994B2

Reaction notes

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