3-Chlorobenzamide → 23589-73-3

HRID 1448671Notes

Reaction equation

HRID 1448671 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].Cl[C:12]([S:14]Cl)=[O:13]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][C:12](=[O:13])[S:14][N:7]=2)[CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 692543-ChlorobenzamideHCID 75990(Chlorothio)formyl chloride

Product 1

HCID 1243739723589-73-3Yield 65.8%

Procedure

m-Chlorobenzamide (75 g, 0.48 mol) and chlorocarbonylsulfenyl chloride (79 g, 0.6 mol, 25% excess) were reacted as described in Example 2 for 1.5 hours. Volatile components were removed under reduced pressure. The dark brown oil was taken up in hot cyclohexane, and the mixture was filtered. Cooling resulted in separation of a dark orange solid. The solid, recrystallized twice from hot ethyl acetate, gave 64.21 g (0.316 mol, 65.8%) of off-white solid, m.p. 83°-84.5°.

Workup

  1. customVolatile components were removed under reduced pressure
  2. filtrationthe mixture was filtered
  3. temperatureCooling
  4. customresulted in separation of a dark orange solid
  5. customThe solid, recrystallized twice from hot ethyl acetate

Sources & evidence

ORD record
ord-19bab1d9b70f4ea99aebabe5944223c7
Source dataset
uspto-grants-1980_02
Patent number
US04187099

Reaction notes

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