Dichloroacetyl chloride → HCID 46916409, compound

HRID 2045927Notes

Reaction equation

HRID 2045927 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.C(N(C(C)C)CC)(C)C.[Cl:27][CH:28]([Cl:32])[C:29](Cl)=[O:30]>C1COCC1.C(OCC)(=O)C>[Cl:27][CH:28]([Cl:32])[C:29]([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:30]

Participants

6

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 46916409HCID 46916409, compoundYield 40.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-quinoxalin-2-ylphenyl)amine (135 mg, 0.610 mmol) and diisopropylethylamine (DIEA, 121 μL, 0.732 mmol) in THF (5 mL), dichloroacetyl chloride (65 μL, 0.673 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 24 hrs and then diluted with ethyl acetate (25 mL). The organic phase was washed with water (25 mL) and then brine (25 mL), dried over MgSO4, and the solvent was evaporated in vacuo to afford 2,2-dichloro-N-[3-(quinoxalin-2-yl)phenyl]acetamide (82 mg, 40% yield). LCMS calculated for C16H11Cl2N3O (M+H): 332.03. found 332.09. 1H-NMR (DMSO-d6, 400, Mhz) δH: 10.60 (1H, br. s), 9.55 (1H, s), 8.53 (1H, s), 8.18-8.05 (3H, m), 7.95-7.85 (3H, m), 7.62 (1H, m), 6.65 (1H, s).

Workup

  1. washThe organic phase was washed with water (25 mL)
  2. dry with materialbrine (25 mL), dried over MgSO4
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-33a5aa65941948bd8b3ec2bb235d7ebe
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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