Thionyl Chloride → HCID 178527431, compound

HRID 1579023Notes

Reaction equation

HRID 1579023 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([Cl:16])[C:5]2[N:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[NH:8][C:4]=2[C:3]=1[S:17]([OH:20])(=O)=[O:18].S(Cl)([Cl:23])=O>CN(C)C=O>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([Cl:16])[C:5]2[N:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[NH:8][C:4]=2[C:3]=1[S:17]([Cl:23])(=[O:20])=[O:18]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178527626HCID 178527626, compound

Product 1

HCID 178527431HCID 178527431, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The 5,6,7-trichloro-2-trifluoromethylbenzimidazole-4-sulphonic acid (155 parts) was added to a stirred mixture of thionyl chloride (770 parts) and dimethylformamide (24 parts). A vigorous effervescence took place, and when this had subsided the mixture was slowly heated to reflux temperature (80°C) and maintained at this temperature for three hours. The reaction mixture was then cooled and the solid crystals filtered off, washed with benzene (160 parts) and dried to give 5,6,7-trichloro-2-trifluoromethylbenzimidazole-4-sulphonyl chloride (138 parts), melting point (with decompoition) 208°-209°C. Evaporation of the filtrate yielded a further 10 parts of the product, giving a total yield of 148 parts (91% yield).

Workup

  1. temperaturewas slowly heated
  2. temperaturemaintained at this temperature for three hours
  3. temperatureThe reaction mixture was then cooled
  4. filtrationthe solid crystals filtered off
  5. washwashed with benzene (160 parts)
  6. customdried

Sources & evidence

ORD record
ord-e156c401d1b6459ca64fe33a2516731b
Source dataset
uspto-grants-1976_02
Patent number
US03940416

Reaction notes

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