N-[4-(3-Chloropropanoyl)phenyl]ethanimidic acid → HCID 86609341, compound

HRID 1712892Notes

Reaction equation

HRID 1712892 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9](NC(=O)C)=[CH:8][CH:7]=1)=[O:5].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CN(C=O)C>[O:21]=[C:19]1[C:18]2[C:17](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16](=[O:26])[N:20]1[CH2:2][CH2:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:18][C:19]([NH2:20])=[O:21])=[CH:10][CH:11]=1)=[O:5]

Participants

4

Reactant 2

HCID 235085N-[4-(3-Chloropropanoyl)phenyl]ethanimidic acidHCID 24194345Phthalimide potassium salt

Product 1

HCID 86609341HCID 86609341, compoundYield 169.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[4-(3-chloro-propionyl)phenyl]acetamide (1.45 g, J. Med. Chem. 8, 1965, 877) and potassium phthalimide (1.31 g) were combined in DMF (5 mL) and heated at 125 C for 30 min, allowed to cool to room temperature diluted with ice water. The suspension was filtered and the filter cake was washed with water and hexanes. The precipitate in a mimimum amount of EtOAc was triturated with hexanes to give 2 g of the title compound. MS (ESI(+)) m/e 337.1 (M+H)+.

Workup

  1. temperatureheated at 125 C for 30 min
  2. filtrationThe suspension was filtered
  3. washthe filter cake was washed with water and hexanes
  4. customThe precipitate in a mimimum amount of EtOAc was triturated with hexanes

Sources & evidence

ORD record
ord-7e495247c4d94bddb508219684d68ede
Source dataset
uspto-grants-2010_09
Patent number
US07795248B2

Reaction notes

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