Ammonia → HCID 19086710, compound

HRID 1464581Notes

Reaction equation

HRID 1464581 reaction equation
[C:1]([C:3]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([O:12][C:13]3[C:18]([F:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=3[Cl:24])=[CH:11][C:5]=2[N+:4]=1[O-])#[N:2].P(Cl)(Cl)Cl.O.N>C(Cl)(Cl)Cl>[C:1]([C:3]1[NH:4][C:5]2[CH:11]=[C:10]([O:12][C:13]3[C:18]([F:19])=[CH:17][C:16]([C:20]([F:22])([F:23])[F:21])=[CH:15][C:14]=3[Cl:24])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 24387Phosphorus trichlorideHCID 178510659HCID 178510659, compound

Product 1

HCID 19086710HCID 19086710, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

2-cyano-5-(2-chloro-4-trifluoromethyl-6-fluorophenoxy)-1H-benzimidazole-3-oxide (0.8 g) was suspended in chloroform (5cm3) stirred and cooled to 5° C. in an ice bath. Phosphorus trichloride (0.25cm ) was added dropwise and when addition was complete the mixture was heated under reflux for 5 minutes. The resulting solution was cooled, water (10cm3) added slowly and the mixture made basic with aqueous ammonia. The organic layer was separated and the aqueous layer extracted twice with chloroform. The combined organic phase was washed with water, dried (MgSO4), filtered and the filtrate evaporated under vacuum. A portion of the residue was purified by preparative plate chromatogrpahy (SiO2 ; ether) to give 2-cyano-5-(2-chloro-4-trifluormethyl-6-fluorophenoxy)benzimidazole as a pale yellow solid, recrystallised from ether/hexane. MS (positive FAB) MH+ =356.

Workup

  1. additionwhen addition
  2. temperaturewas heated
  3. temperatureunder reflux for 5 minutes
  4. temperatureThe resulting solution was cooled
  5. customThe organic layer was separated
  6. extractionthe aqueous layer extracted twice with chloroform
  7. washThe combined organic phase was washed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe filtrate evaporated under vacuum
  11. customA portion of the residue was purified by preparative plate chromatogrpahy (SiO2 ; ether)

Sources & evidence

ORD record
ord-b5bf6b85e7274fa491508515367d270d
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

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