Tetrahydrofuran → 4-Nitro-1H-benzo[d]imidazol-2(3H)-one

HRID 1505153Notes

Reaction equation

HRID 1505153 reaction equation
[N+:1]([C:4]1[C:5]([NH2:11])=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1C[O:15][CH2:14]C1>CCOC(C)=O>[N+:1]([C:4]1[C:5]2[NH:11][C:14](=[O:15])[NH:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 41498284-Nitro-1H-benzo[d]imidazol-2(3H)-oneYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To 3-nitro-1,2-phenylenediamine 3a (2 g, 13.06 mmol) dissolved in THF (50 ml) was added in one portion DCI (1.5 equiv., 19.6 mmol, 3.176 g) and the reaction was refluxed for 2 hours. (TLC AcOEt 1/petroleum ether 1). The reaction was filtrated and the yellow solid material was washed with THF and diethyl ether obtaining 2 g of the product that was used for the following step without further purification. Yield=88% 1HNMR (DMSO, 200 MHz) δ 7.11 (1H, t, J=7.6 Hz), 7.31 (1H, dd, J=7.8 Hz, J′=1.2 Hz), 7.74 (1H, dd, J=8.6 Hz, J′=1 Hz), 11.45 (2H, bs)

Workup

  1. additionwas added in one portion DCI (1.5 equiv., 19.6 mmol, 3.176 g)
  2. temperaturethe reaction was refluxed for 2 hours
  3. filtrationThe reaction was filtrated
  4. washthe yellow solid material was washed with THF and diethyl ether obtaining 2 g of the product that
  5. customwas used for the following step without further purification

Sources & evidence

ORD record
ord-53c183bfeb8f45cb9dbc64218db621e8
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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