N-methyl-2-pyrrolidone → HCID 9885625, compound

HRID 2084992Notes

Reaction equation

HRID 2084992 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5](/[CH:6]=[CH:7]/[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.Cl[C:14]1[C:15](=[O:27])[NH:16][C:17](=[O:26])[C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.CN1CCCC1=O>Cl>[C:8](/[CH:7]=[CH:6]/[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:14]2[C:15](=[O:27])[NH:16][C:17](=[O:26])[C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 1549514p-Aminocinnamic acidHCID 112879523-chloro-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione

Product 1

HCID 9885625HCID 9885625, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of trans-4-aminocinnamic acid (0.205 g, 1.26 mmol), 3-chloro-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione (0.123 g, 0.51 mmol) and 1-methyl-2-pyrrolidinone (1.0 mL) was heated in a sealed tube in a hotblock set at 69° C., for 28.5 hours. The mixture was diluted with aqueous hydrochloric acid (10 mL) and extracted with ethyl acetate (2×20 mL). The combined organics were washed with brine (2×10 mL), dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was triturated with a mixture of dichloromethane and ethyl acetate to afford the title compound as a solid.

Workup

  1. temperaturewas heated in a sealed tube in a hotblock
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. washThe combined organics were washed with brine (2×10 mL)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated to dryness
  6. customThe residue was triturated with a mixture of dichloromethane and ethyl acetate

Sources & evidence

ORD record
ord-e6cdf01662ce49daa24c868417bf78ec
Source dataset
uspto-grants-2004_04
Patent number
US06719520B2

Reaction notes

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