Dichloromethane → HCID 22137861, compound

HRID 858324Notes

Reaction equation

HRID 858324 reaction equation
[CH2:1]([Cl:3])Cl.Br[CH2:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([NH:19][C:20](=[O:23])[CH2:21]Br)[CH:10]=1)=[O:7].[Cl:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28]>C(OCC)(=O)C>[Cl:24][C:25]1[CH:26]=[C:27]([NH:28][CH2:5][C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([NH:19][C:20](=[O:23])[CH2:21][NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:1]([Cl:3])[CH:14]=3)[CH:10]=2)=[O:7])[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 79323-ChloroanilineHCID 22137858HCID 22137858, compound

Product 1

HCID 22137861HCID 22137861, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a CH2Cl2 solution of 2-Bromo-N-[3-(2-bromo-acetylamino)-5-trifluoromethyl-phenyl]-acetamide (150 mg, 0.30 mmol) at room temperature was added 3-chloroaniline (100 μL), the mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate, washed with NaHCO3 solution followed by 1 N HCl (2×) and brine. The organic layer was dried over MgSO4, filtered and stripped and the crude product was purified by flash chromatography on silica gel eluted with hexane/ethyl acetate (2:1) to give 132 mg of the title compound in 92% yield. 1H NMR (400 MHz, CDCl3): δ 3.87(s, 4H), 6.49(dd, J=2, 8.4 Hz, 2H), 6.63(s, 2H), 6.79(d, J=2, 8.4 Hz, 2H), 7.10(t, J=8.0 Hz, 2H), 7.46(s, 2H), 8.20(s, 1H), 8.77(s, 2H). MS SEI m/z relative intensity:M+H, 511.2(100).

Workup

  1. washwashed with NaHCO3 solution
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe crude product was purified by flash chromatography on silica gel
  5. washeluted with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-8154c1a2d9b44ca3a4e209fbf9bf5dcc
Source dataset
uspto-grants-2006_12
Patent number
US07148259B1

Reaction notes

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