N-bromobutanimide → HCID 70171800, compound

HRID 716710Notes

Reaction equation

HRID 716710 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[O:12][CH:13]=2)=[CH:5][CH:4]=1.[Br:27]N1C(=O)CCC1=O>ClCCl.C(Cl)(Cl)Cl>[Br:27][C:13]1[O:12][C:11]([CH:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]2)=[N:10][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 71207840HCID 71207840, compound

Product 1

HCID 70171800HCID 70171800, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

tert-butyl 4-{4-[4-(methylsulfanyl)phenyl]-1,3-oxazol-2-yl}piperidine-1-carboxylate (585 mg, 1.56 mmol) was dissolved in dichloromethane (15.6 mL) under argon atmosphere. N-bromosuccinimide (306 mg, 1.72 mmol) was added portionwise as a solid to the stifling solution. The resulting solution stirred at 25° C. for 6 hours. The solution was then diluted with chloroform and washed with aqueous sodium bisulfite. The organics were dried over sodium sulfate and concentrated in vacuo to yield 680 mg of the desired product as yellow oil. LCMS (M+1)=453.40

Workup

  1. washwashed with aqueous sodium bisulfite
  2. dry with materialThe organics were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9ef860370ea41e39a043b956048153e
Source dataset
uspto-grants-2015_11
Patent number
US09193697B2

Reaction notes

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