Thionyl Chloride → HCID 178526751, compound

HRID 437401Notes

Reaction equation

HRID 437401 reaction equation
O[N:2]1[C:6]2[CH:7]=[C:8]([N+:14]([O-:16])=[O:15])[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=2[N:4]=[C:3]1[C:17]([F:20])([F:19])[F:18].S(Cl)([Cl:23])=O>CN(C)C=O.O>[Cl:23][C:7]1[C:6]2[N:2]=[C:3]([C:17]([F:20])([F:19])[F:18])[NH:4][C:5]=2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 21428401HCID 21428401, compound

Product 1

HCID 178526751HCID 178526751, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 962WaterSolvent

Procedure

Crude 1-hydroxy-4,6-dinitro-2 -(trifluoromethyl)-benzimidazole (about 5 grams) was mixed with about 50 milliliters of thionyl chloride and several drops of dimethylformamide added. The reaction mixture was stirred overnight, then poured slowly into water and filtered. The solid was dissolved in benzene and eluted off a silica column with benzene. As a result of the foregoing operations, the desired 7-chloro-4,6-dinitro-2-(trifluoromethyl) benzimidazole product was obtained, m.p., 189° -91° C.

Workup

  1. additionadded
  2. filtrationfiltered
  3. dissolutionThe solid was dissolved in benzene
  4. washeluted off a silica column with benzene
  5. customAs a result of the foregoing operations

Sources & evidence

ORD record
ord-c8b2297f0570401684207650a7089511
Source dataset
uspto-grants-1977_06
Patent number
US04031107

Reaction notes

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