Acetyl chloride → 5-Chloroisatoic anhydride

HRID 227554

Reaction equation

HRID 227554 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7](Cl)[C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13](OCC)=[O:14].C([Cl:21])(=O)C>O1CCOCC1>[Cl:21][C:8]1[CH:7]=[C:3]2[C:4]([O:6][C:13](=[O:14])[NH:1][C:2]2=[CH:10][CH:9]=1)=[O:5]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10928Ethyl chloroformateHCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 784805-Chloroisatoic anhydrideYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

2-Amino-6-chlorobenzoic acid (30 g) was suspended in 1,4-dioxane (225 ml) and ethyl chloroformate (75 ml) was added. The mixture was heated at reflux for 1 hour, then cooled to 50° C., and acetyl chloride (75 ml) was added. The mixture was stirred for 10 hours, after which the precipitated product was filtered off and washed with toluene. Drying in vacuum yields 5-chloroisatoic anhydride (33 g, 97% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. filtrationafter which the precipitated product was filtered off
  4. washwashed with toluene
  5. customDrying in vacuum

Sources & evidence

ORD record
ord-95d444a5725d4f3d89bff7eb6a69388c
Source dataset
uspto-grants-2009_07
Patent number
US07560557B2

Linked notes

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