Tetrahydrofuran → 1-(1-methyl-1H-benzo[d]imidazol-5-yl)propan-1-one

HRID 626243

Reaction equation

HRID 626243 reaction equation
CON(C)[C:4]([C:6]1[CH:15]=[CH:14][C:9]2[N:10]([CH3:13])[CH:11]=[N:12][C:8]=2[CH:7]=1)=[O:5].[CH2:17]1COC[CH2:18]1>>[CH3:13][N:10]1[C:9]2[CH:14]=[CH:15][C:6]([C:4](=[O:5])[CH2:17][CH3:18])=[CH:7][C:8]=2[N:12]=[CH:11]1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 86665700N-methoxy-N,1-dimethyl-1H-benzo[d]imidazole-5-carboxamide

Product 1

HCID 391039641-(1-methyl-1H-benzo[d]imidazol-5-yl)propan-1-oneYield 94%

Procedure

To a solution of N-methoxy-N,1-dimethyl-1H-benzo[d]imidazole-5-carboxamide (900 mg, 1.0 eq) in 30 mL anhydrous THF was added 3 M EtBrMg (9 mL, 6.0 eq) slowly at 0° C. The reaction was stirred at rt overnight, quenched with sat NH4Cl (aq), and extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (730 mg, 94%). 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 8.04 (J=8.4 Hz, 1.6 Hz, 1H), 7.95 (s, 1H), 7.43 (d, J=8.4 Hz, 1H), 3.89 (s, 3H), 3.10 (q, J=7.2 Hz, 2H), 1.27 (t, J=7.2 Hz, 3H).

Workup

  1. customquenched with sat NH4Cl (aq)
  2. extractionextracted with CH2Cl2
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-1a559c9705084fb5ba1aa4491ffb4216
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Linked notes

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