Sodium hydride → HCID 66749106, compound

HRID 882192Notes

Reaction equation

HRID 882192 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1.[H-].[Na+].I[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:8](=[O:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 84953Propane, 1-iodo-2,2-dimethyl-HCID 98159826-broMo-1-Methyl-1H-benzo[d]iMidazol-2(3H)-one

Product 1

HCID 66749106HCID 66749106, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (1-4, 500 mg, 2.20 mmol) in DMF (10 ml) was treated with Sodium hydride (176 mg, 4.40 mmol, 2.0 eq) followed by the 1-Iodo-2,2-Dimethylpropane (585 pt, 4.40 mmol, 2.0 eq). The reaction was irradiated at 175 deg C. for 20 min in a microwave. The reaction was complete by LC/MS, so it was partitioned between EtOAc (2×125 ml) and water (150 ml). The combined organic layers were dried over Na2SO4 and concentrated. The crude maroon-orange oil was purified via flash column chromatography (SiO2: 100% Hex to 60:40 Hex:EtOAc), affording the title compound, 5-bromo-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (1-5), as a yellow solid with >95% purity. 1H NMR (600 MHz, CDCl3) δ 7.18 (dd, 1H, J=Hz), 7.10 (s, 1H), 6.88 (d, 1H, J=Hz), 3.63 (s, 2H), 3.40 (s, 3H), 1.02 (s, 9H). LRMS m/z: Calc'd for C7H7BrN2O2 (M+H) 232.1, found 232.8.

Workup

  1. customThe reaction was irradiated at 175 deg C
  2. customwas partitioned between EtOAc (2×125 ml) and water (150 ml)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude maroon-orange oil was purified via flash column chromatography (SiO2: 100% Hex to 60:40 Hex:EtOAc)

Sources & evidence

ORD record
ord-767c989ea59f4bd0b406a017a090f491
Source dataset
uspto-grants-2015_03
Patent number
US08993779B2

Reaction notes

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