Thionyl Chloride → 2-acetoxy 4-acetamino 5-chlorobenzoyl Chloride

HRID 256334Notes

Reaction equation

HRID 256334 reaction equation
S(Cl)([Cl:3])=O.[C:5]([O:8][C:9]1[CH:17]=[C:16]([NH:18][C:19]([CH3:21])=[O:20])[C:15]([Cl:22])=[CH:14][C:10]=1[C:11](O)=[O:12])(=[O:7])[CH3:6]>>[C:5]([O:8][C:9]1[CH:17]=[C:16]([NH:18][C:19]([CH3:21])=[O:20])[C:15]([Cl:22])=[CH:14][C:10]=1[C:11]([Cl:3])=[O:12])(=[O:7])[CH3:6]

Participants

3

Reactant 2

HCID 24386Thionyl Chloride2×HCID 198486102-Acetoxy 4-acetamino 5-chlorobenzoic acid2×

Product 1

HCID 201637762-acetoxy 4-acetamino 5-chlorobenzoyl Chloride

Procedure

501 g of thionyl chloride and 71.5 g of 2-acetoxy 4-acetamino 5-chlorobenzoic acid were introduced into a two liter balloon flask provided with a reflux condenser. Heating was effected by a water bath under reflux until dissolution of reactants occurred. Some cooling was applied and 71.5 g of 2-acetoxy 4-acetamino 5chlorobenzoic acid was added. Heating was effected as before under reflux for a period of 1 hour, but without causing the acid to dissolve. 63 g of thionyl chloride was added. The acid dissolved immediately, and an acid chloride quickly crystallized.

Workup

  1. customprovided with a reflux condenser
  2. temperatureHeating
  3. customwas effected by a water bath
  4. temperatureunder reflux until dissolution of reactants
  5. temperatureHeating
  6. temperatureunder reflux for a period of 1 hour
  7. dissolutionto dissolve
  8. dissolutionThe acid dissolved immediately
  9. customan acid chloride quickly crystallized

Sources & evidence

ORD record
ord-c6ff9b635a52493a9c3fb8490dcdfd10
Source dataset
uspto-grants-1987_10
Patent number
US04703055

Reaction notes

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