N-bromobutanimide → HCID 69025577, compound

HRID 1866760Notes

Reaction equation

HRID 1866760 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=1[NH2:13].[Br:14]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Br:14][C:10]1[CH:9]=[C:8]([CH3:12])[C:7]([NH2:13])=[C:6]([C:2]2[NH:3][CH2:4][CH2:5][N:1]=2)[CH:11]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 451209702-(4,5-Dihydro-1H-imidazol-2-yl)-6-methylaniline

Product 1

HCID 69025577HCID 69025577, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the title compound of Step B (0.38 g, 2.17 mmol) in N,N-dimethylformamide (10 mL) was added N-bromosuccinimide (0.38 g, 2.13 mmol) and the mixture was stirred at ambient temperature for 1 hour. Additional N-bromosuccinimide (0.06 g, 0.34 mmol) was added and the mixture stirred for an additional 0.5 hour before being diluted with ethyl acetate and washed three times with water. The combined aqueous fractions were extracted with ethyl acetate and the organic layer was washed with water. The combined organic fractions were dried (magnesium sulfate), concentrated and purified by flash column chromatography (silica gel, 2% then 5% methanol in dichloromethane) to give the title compound of Step C (94 mg) as a light brown oil.

Workup

  1. stirringthe mixture stirred for an additional 0.5 hour
  2. washwashed three times with water
  3. extractionThe combined aqueous fractions were extracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. dry with materialThe combined organic fractions were dried (magnesium sulfate)
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel, 2%

Sources & evidence

ORD record
ord-38757773996b4007a2dd4564e6ed31c9
Source dataset
uspto-grants-2009_12
Patent number
US07629463B2

Reaction notes

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