Formamide → 4-Chloro-phthalimide

HRID 1792954Notes

Reaction equation

HRID 1792954 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=O)[O:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.O.C([NH2:16])=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:8])[NH:16][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 962WaterHCID 670444-Chlorophthalic anhydride

Product 1

HCID 2312394-Chloro-phthalimideYield 104.6%

Conditions

Temperature
20 °C

Procedure

A solution of 10.0 g of 4-chlorophthalic anhydride in 24.6 g of formamide is heated at a temperature in the region of 120° C. with stirring for 3 hours and is then cooled to a temperature in the region of 20° C. and poured into 100 cm3 of water. After stirring for 30 minutes, the mixture is filtered and the precipitate is then dried under vacuum at a temperature in the region of 60° C. 10.4 g of 4-chlorophthalimide are thus obtained in the form of a solid melting at 171° C. Rf=0.07 (thin layer chromatography on silica gel, eluent: dichloromethane).

Workup

  1. stirringAfter stirring for 30 minutes
  2. filtrationthe mixture is filtered
  3. customthe precipitate is then dried under vacuum at a temperature in the region of 60° C

Sources & evidence

ORD record
ord-a119c77f3fcb488fb7c2f4d718a10521
Source dataset
uspto-grants-2006_07
Patent number
US07078428B2

Reaction notes

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