Ammonia → HCID 178423969, compound

HRID 1007123Notes

Reaction equation

HRID 1007123 reaction equation
O[C:2]1[NH:3][C:4]2[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.P(Cl)(Cl)([Cl:14])=O.N>O>[Cl:14][C:2]1[NH:3][C:4]2[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178424002HCID 178424002, compound

Product 1

HCID 178423969HCID 178423969, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Hydroxy-4-methylbenzimidazole (5.92 g, 40 mmol) and 40 mL of phosphoryl chloride are introduced into a 250 mL two-necked flask under an argon atmosphere, with magnetic stirring. The mixture is refluxed for 20 hours and the phosphoryl chloride is evaporated off under vacuum. The solid obtained is taken up in water (250 mL), neutralized to pH=8 with 28% aqueous ammonia and the aqueous phase is extracted with ethyl acetate (3×250 mL). After the usual work-up, the title product is obtained in a yield of 93% (6.23 g). 1H NMR (300 MHz, δ ppm) DMSO D6: 2.47 (s, 3H), 7.01 (d, 1H), 7.11 (t, 1H), 7.32 (d, 1H).

Workup

  1. temperatureThe mixture is refluxed for 20 hours
  2. customthe phosphoryl chloride is evaporated off under vacuum
  3. customThe solid obtained
  4. extractionthe aqueous phase is extracted with ethyl acetate (3×250 mL)

Sources & evidence

ORD record
ord-4dbc76571e5c481eb6fd897c1907879b
Source dataset
uspto-grants-2004_09
Patent number
US06794382B2

Reaction notes

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