Sodium hydride → HCID 66748876, compound

HRID 882200Notes

Reaction equation

HRID 882200 reaction equation
F[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][CH3:13])=[O:11].[H-].[Na+]>CN(C=O)C>[I:8][C:6]1[CH:7]=[CH:2][C:3]2[NH:9][C:10](=[O:11])[N:12]([CH3:13])[C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 597173511-(2-Fluoro-4-iodophenyl)-3-methylurea

Product 1

HCID 66748876HCID 66748876, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(2-fluoro-4-iodophenyl)-N′-methylurea (6-2, 2.9 g, 9.86 mmol) in DMF (12 ml) were treated with Sodium Hydride (308 mg, 12.8 mmol, 1.3 eq). The reaction mixture was irradiated in a microwave at 200 deg C. for 10 min. The starting material was consumed, so it was partitioned between EtOAc (2×75 ml) and water (85 ml), and the combined organic layers were dried over Na2SO4 and concentrated. The residual crude maroon oil was purified via flash column chromatography (SiO2: 100% Hex to 50:50 Hex/EtOAc), which afforded the title compound, 6-iodo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (6-3), as a tan solid. 1H NMR (500 MHz, CDCl3) δ 9.64 (bs, 1H), 7.39 (d, 1H, J=6.6 Hz), 7.30 (s, 1H), 6.87 (d, 1H, J=8.1 Hz), 3.39 (s, 3H). LRMS m/z: Calc'd for C8H7IN2O (M+H) 275.1, found 274.9.

Workup

  1. customThe reaction mixture was irradiated in a microwave at 200 deg C
  2. customThe starting material was consumed, so it
  3. customwas partitioned between EtOAc (2×75 ml) and water (85 ml)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residual crude maroon oil was purified via flash column chromatography (SiO2: 100% Hex to 50:50 Hex/EtOAc), which

Sources & evidence

ORD record
ord-0f15cc79e52148db913bd7926182adcd
Source dataset
uspto-grants-2015_03
Patent number
US08993779B2

Reaction notes

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