Chloroform → Methyl 4-amino-3,5-dichlorobenzoate

HRID 1441041Notes

Reaction equation

HRID 1441041 reaction equation
[NH2:1][C:2]1C=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.S(Cl)([Cl:15])(=O)=O.[OH-].[Na+].[CH:19]([Cl:22])(Cl)Cl>>[NH2:1][C:2]1[C:3]([Cl:15])=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:19]=1[Cl:22]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 12082Methyl 4-aminobenzoateHCID 14798Sodium HydroxideHCID 24648Sulfuryl chloride2×

Product 1

HCID 604808Methyl 4-amino-3,5-dichlorobenzoate

Procedure

Methyl 4-aminobenzoate (25 g.) in dry chloroform (250 ml.) was treated dropwise with sulphuryl chloride (10 ml.) and the mixture heated at reflux for 4 hours. A further supply of sulphuryl chloride (10 ml.) was added and heating continued for a further 2 hours. The reaction mixture was poured onto ice and 2N sodium hydroxide solution was added. The organic solution was separated and the aqueous phase extracted with ethyl acetate. The combined organic solution was dried (anhydrous magnesium sulphate) and evaporated to give methyl 4-amino-3,5-dichlorobenzoate as a solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 4 hours
  3. temperatureheating
  4. additionwas added
  5. customThe organic solution was separated
  6. extractionthe aqueous phase extracted with ethyl acetate
  7. dry with materialThe combined organic solution was dried (anhydrous magnesium sulphate)
  8. customevaporated

Sources & evidence

ORD record
ord-d5b8192b3b144b0399836676248d826a
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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