Phosphorus oxychloride → HCID 178526406, compound

HRID 1521359Notes

Reaction equation

HRID 1521359 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]2[NH:6][C:7](=O)[NH:8][C:4]=2[CH:3]=1.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:7]1[NH:8][C:4]2[CH:3]=[C:2]([Cl:1])[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]=2[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 145662265-Chloro-1,3-dihydro-6-nitro-2H-benzimidazol-2-one

Product 1

HCID 178526406HCID 178526406, compoundYield 89%

Conditions

Temperature
85 °C

Procedure

To 5-chloro-6-nitro-1,3-dihydro-benzoimidazol-2-one (5.63 g, 26.35 mmol) was added phosphorus oxychloride (35 mL) and the reaction mixture was heated to 85° C. for 36 h. The reaction mixture was concentrated and the residue triturated with cold saturated aqueous sodium bicarbonate (to pH 8, 0.8 L). The resulting precipitate was collected and dried to yield the titled compound (5.43 g, 89% yield). MS (ESI/CI): mass calcd. for C7H3Cl2N3O2, 231.0; m/z found, 232.0 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue triturated with cold saturated aqueous sodium bicarbonate (to pH 8, 0.8 L)
  3. customThe resulting precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-b796a6adb6a84f0d9bc8c842c0342adf
Source dataset
uspto-grants-2015_07
Patent number
US09073923B2

Reaction notes

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