Ammonia → 2,5,6-Trichloro-1H-benzimidazole

HRID 1985813Notes

Reaction equation

HRID 1985813 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]2[NH:6][C:7](=O)[NH:8][C:4]=2[CH:3]=1.O.N.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:7]1[NH:6][C:5]2[CH:10]=[C:11]([Cl:12])[C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 24813Phosphorus oxychlorideHCID 98991485,6-Dichloro-1,3-Dihydro-2H-Benzimidazol-2-One

Product 1

HCID 2860092,5,6-Trichloro-1H-benzimidazole

Conditions

Temperature
120 °C

Procedure

5,6-Dichloro-1,3-dihydro-2H-benzimidazol-2-one (11.5 g) was suspended in phosphorus oxychloride (40 mL), and the mixture was stirred at 120° C. for 24 hours. After cooling the reaction mixture, water was added to the reaction mixture, and to the mixture was added 28% aqueous ammonia solution to alkalize. The solid was collected by filtration and dried to give the title compound (5.0 g).

Workup

  1. additionwas added to the reaction mixture
  2. filtrationThe solid was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-bc598925104f453987465d0b8329aae8
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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