Chlorosuccinimide → HCID 59857382, compound

HRID 555406Notes

Reaction equation

HRID 555406 reaction equation
[Cl:1]N1C(=O)CCC1=O.[C:9]([C:13]1[CH:26]=[CH:25][CH:24]=[CH:23][C:14]=1[O:15][C:16]1[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][N:17]=1)([CH3:12])([CH3:11])[CH3:10]>CN(C=O)C>[C:9]([C:13]1[CH:26]=[CH:25][CH:24]=[CH:23][C:14]=1[O:15][C:16]1[C:21]([NH2:22])=[CH:20][CH:19]=[C:18]([Cl:1])[N:17]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 286054272-(2-Tert-butylphenoxy)pyridin-3-amine

Product 1

HCID 59857382HCID 59857382, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of N-chlorosuccinimide (556 mg, 4.2 mmol) in DMF (10 ml) was added to a solution of 1b (960 mg, 4.0 mmol) in DMF (15 ml) at rt. The reaction was heated at 40° C. for 30 min. The reaction mixture was cooled to rt and the reaction was quenched with saturated aqueous sodium thiosulfate (Na2S2O3) solution (100 mL). The mixture was extracted with ethyl acetate (3×20 ml) and the organic layers were washed with aqueous sodium thiosulfate solution, brine and were dried over sodium sulfate. The solvents were removed under reduced pressure and the dark red oil was purified by chromatography on silica (continuous gradient 0 to 40% Hexane/EtOAc) to give 125a as an off-white solid (746 mg, 68% yield). [M+H]+=277.11. 1H NMR (500 MHz, CDCl3): 7.41 (d, 1H, J=7.4 Hz), 7.20 (t 1H, J=7.4 Hz), 7.11 (t, 1H, J=7.4 Hz), 7.01 (d, 1H, J=8.1 Hz), 6.93 (d, 1H, J=8.1 Hz), 6.85 (d, 1H, J=8.1 Hz), 3.91 (s, 1H), 1.39 (s, 9H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customthe reaction was quenched with saturated aqueous sodium thiosulfate (Na2S2O3) solution (100 mL)
  3. extractionThe mixture was extracted with ethyl acetate (3×20 ml)
  4. washthe organic layers were washed with aqueous sodium thiosulfate solution, brine
  5. dry with materialwere dried over sodium sulfate
  6. customThe solvents were removed under reduced pressure
  7. customthe dark red oil was purified by chromatography on silica (continuous gradient 0 to 40% Hexane/EtOAc)

Sources & evidence

ORD record
ord-ce4159f343824ee292969289e0490d05
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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