Chloroacetyl chloride → 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide

HRID 2045911Notes

Reaction equation

HRID 2045911 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.CCN(CC)CC.[Cl:25][CH2:26][C:27](Cl)=[O:28]>C1COCC1>[Cl:25][CH2:26][C:27]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:12]=1)=[O:28]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 14854332-chloro-N-(3-quinoxalin-2-ylphenyl)acetamideYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-quinoxalin-2-ylphenyl)amine (4.43 g, 20 mmol) and Et3N (3 mL, 22 mmol) in THF (100 mL), chloroacetyl chloride (1.6 mL, 20 mmol) was added dropwise with stirring. The solvent was evaporated in vacuo. The residue was slurred with water, filtered, and dried. The solid was dissolved in hot toluene (300 mL), treated with silica gel, filtered and left to recrystallize to afford 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (4.5 g, 76% yield). LCMS calculated for C16H12ClN3O (M+H): 298.75. found 298.06. 1H-NMR (400 MHz, DMSO-d6) δH: 10.6 (1H, br. s), 9.52 (1H, s), 8.54 (1H, m), 8.20-8.05 (3H, m), 7.90-7.70 (3H, m), 7.62-7.51 (1H, m), 4.31 (2H, s).

Workup

  1. customThe solvent was evaporated in vacuo
  2. filtrationfiltered
  3. customdried
  4. dissolutionThe solid was dissolved in hot toluene (300 mL)
  5. additiontreated with silica gel
  6. filtrationfiltered
  7. waitleft
  8. customto recrystallize

Sources & evidence

ORD record
ord-fe42dc97f9834dd9a159a9d57901cdba
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

Loading…