Water → HCID 21876312, compound

HRID 724179Notes

Reaction equation

HRID 724179 reaction equation
[Cl:1][C:2]1[C:3]([C:21]([F:24])([F:23])[F:22])=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1CCO.N1[CH:30]=[CH:29]C=CC=1.[C:31](Cl)(=[O:33])[CH3:32].[OH2:35]>ClCCl>[C:31]([O:33][CH2:29][CH2:30][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:6]2[CH:17]=[C:2]([Cl:1])[C:3]([C:21]([F:24])([F:22])[F:23])=[CH:4][C:5]=2[N+:18]([O-:20])=[O:19])=[CH:9][CH:10]=1)(=[O:35])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 21876194HCID 21876194, compound

Product 1

HCID 21876312HCID 21876312, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-(4-{[5-chloro-2-nitro-4-(trifluoromethyl)phenyl]amino}phenyl)ethanol (Example 104, step 1, 8.1 g, 22.4 mmol) and pyridine (1.8 ml, 22.45 mmol) in dichloromethane (200 ml) was added acetyl chloride (1.6 ml, 22.4 mmol) at 0° C. The mixture was stirred at 0° C. for 45 min. The mixture was added water (50 ml) and extracted with dichloromethane (300 ml). The organic layer was washed with brine (100 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with hexane/ethyl acetate (2:1) to afford 8.6 g (95%) of the title compound as yellow solids.

Workup

  1. extractionextracted with dichloromethane (300 ml)
  2. washThe organic layer was washed with brine (100 ml)
  3. dry with materialdried (Na2SO4)
  4. customAfter removal of solvent
  5. customthe crude product was purified by flash column chromatography
  6. washeluting with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-40c9e7b4e43d418d889a117dbd736176
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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