N-bromobutanimide → HCID 59857539, compound

HRID 555405Notes

Reaction equation

HRID 555405 reaction equation
[Br: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.O>[Br:1][C:18]1[N:17]=[C:16]([O:15][C:14]2[CH:23]=[CH:24][CH:25]=[CH:26][C:13]=2[C:9]([CH3:12])([CH3:10])[CH3:11])[C:21]([NH2:22])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 286054272-(2-Tert-butylphenoxy)pyridin-3-amine

Product 1

HCID 59857539HCID 59857539, compoundYield 104.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-bromosuccinimide (2.32 g, 13.0 mmol) in DMF (20 ml) was added to a cold (−20° C.) solution of 1b (2.76 g, 11.4 mmol) in DMF (25 ml). The reaction rapidly turned dark red. HPLC analysis after 5 min showed that the reaction was complete. The reaction was quenched with a freshly prepared solution of sodium thiosulfate (40 ml, 10% aqueous). A precipitate formed. The mixture was warmed to rt and was diluted with water (60 ml). The solid was filtered, washed with water and dried overnight under reduced pressure to give 123a (3.82 g, 96% yield) as brown solid. [M+H]+=321.14. 1H NMR (500 MHz, CDCl3) δ ppm 1.40 (s, 9H), 3.91 (s, 2H), 6.93 (m, 2H), 7.00 (d, J=8.07 Hz, 1H), 7.12 (t, J=7.73 Hz, 1H), 7.20 (t, J=7.73 Hz, 1H), 7.41 (d, J=8.07 Hz, 1H).

Workup

  1. customThe reaction rapidly turned dark red
  2. customThe reaction was quenched with a freshly prepared solution of sodium thiosulfate (40 ml, 10% aqueous)
  3. customA precipitate formed
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried overnight under reduced pressure

Sources & evidence

ORD record
ord-43bfd150c47f45a2be06e1abddfaa04d
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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