N-bromobutanimide → HCID 12348631, compound

HRID 1506805Notes

Reaction equation

HRID 1506805 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:13]=[CH:14][CH:15]=1>ClCCl.O>[Br:1][C:19]1[S:18][C:17]([NH:16][C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([Cl:9])[CH:11]=2)=[N:21][CH:20]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 12348627HCID 12348627, compound

Product 1

HCID 12348631HCID 12348631, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

N-Bromosuccinimide (7.60 g, 42.7 mmol) was added to a solution of 26B (10 g, 47.5 mmol) in dichloromethane (150 mL), and the mixture was stirred at room temperature for 0.16 h. The reaction mixture was diluted with dichloromethane and water, separated organic layer was dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography using 15% ethyl acetate in hexane to afford the title compound (2.54 g, 18%) as pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.54 (s, 1H), 7.87 (t, J=2.0 Hz, 1H), 7.41-7.26 (m, 3H), 7.01 (dt, J1=7.3 Hz, J2=1.8 Hz, 1H). ESI-MS m/z: 291 (M+H)+.

Workup

  1. customseparated organic layer
  2. dry with materialwas dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-af2a309bda3842048d9614bffa674aad
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

Loading…