N-bromobutanimide → HCID 58994403, compound

HRID 1508027Notes

Reaction equation

HRID 1508027 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH2:12])=[O:11])=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)Cl.CC#N.[Cl-].[Na+].O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([NH2:12])=[O:11])=[CH:6][C:7]=1[Br:13]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 135960744-AMino-benzenepropanaMide

Product 1

HCID 58994403HCID 58994403, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 21877088Acetonitrile methylene chlorideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 3-(4-amino-phenyl)-propionamide (as prepared in the previous step, 123 mg, 0.749 mmol) in 10 mL of 1:1 DCM/CH3CN at 0° C. was added N-bromosuccinimide (NBS) (133 mg, 0.749 mmol) in 4 mL of 1:1 DCM/CH3CN. The mixture was warmed to RT and stirred for 1 h under Ar. Treated with 20 mL of brine, the mixture was extracted with EtOAc (3×20 mL). The combined organic layers were concentrated in vacuo and the residue was purified by flash chromatography on silica gel (1-4% MeOH/DCM) giving 133 mg (81%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C9H11BrN2O, 243.0 (M+H). found 242.9.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×20 mL)
  2. concentrationThe combined organic layers were concentrated in vacuo
  3. customthe residue was purified by flash chromatography on silica gel (1-4% MeOH/DCM)

Sources & evidence

ORD record
ord-cc572fca35e94394945b44924f67906c
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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