N-bromobutanimide → HCID 118044990, compound

HRID 922591Notes

Reaction equation

HRID 922591 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[S:13][C:14]([CH3:21])=[CH:15][C:16]=1[C:17]([O:19][CH3:20])=[O:18].[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:22][CH2:21][C:14]1[S:13][C:12]([N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])=[C:16]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 118045074HCID 118045074, compound

Product 1

HCID 118044990HCID 118044990, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of protected 2-aminothiophene 14 (2.5 g; 8.33 mmol), N-bromosuccinimide (1.55 g; 8.74 mmol) and benzoyl peroxide (20 mg) in CCl4 (50 ml) was heated at reflux temperature for 20 h under argon atmosphere. The CCl4 was evaporated under reduced pressure and the residue was extracted with dichloromethane (3×50 ml). The combined organic phases were washed with a saturated solution of NaHCO3, dried over magnesium sulfate and the solvent was evaporated under reduced pressure Purification by column chromatography (silica, eluent CH2Cl2) afforded 15 (1.9 g, 60%) as an off-white solid. 1H NMR (300 MHz, CDCl3) δH 3.72 (s, 3H); 4.66 (s, 2H); 7.51 (s, 1H); 7.84 (m, 2H); 7.97 (m, 2H).

Workup

  1. temperatureat reflux temperature for 20 h under argon atmosphere
  2. customThe CCl4 was evaporated under reduced pressure
  3. extractionthe residue was extracted with dichloromethane (3×50 ml)
  4. washThe combined organic phases were washed with a saturated solution of NaHCO3
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure Purification by column chromatography (silica, eluent CH2Cl2)

Sources & evidence

ORD record
ord-d291eee7cfd54ce5ae8264b0177e8155
Source dataset
uspto-grants-2016_03
Patent number
US09278958B2

Reaction notes

Loading…