Bromoacetyl bromide → HCID 58577474, compound

HRID 587429Notes

Reaction equation

HRID 587429 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[N:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)C(C)C)(C)C.Br[CH2:30][C:31](Br)=[O:32]>C1COCC1.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:11]3=[N:12][C:13]4[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=4[N:15]3[C:31](=[O:32])[CH2:30]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 61147Bromoacetyl bromideHCID 81531DiisopropylethylamineHCID 5219340N-(4-nitrophenyl)-1H-benzimidazol-2-amine

Product 1

HCID 58577474HCID 58577474, compoundYield 8.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of N-(4-nitrophenyl)-1H-benzimidazol-2-amine (947 mg) and N,N-diisopropylethylamine (1.45 g) in THF (10 mL) at −78° C. was treated dropwise with a solution of bromoacetyl bromide (826 mg) in THF (2.0 mL) then the resulting mixture was allowed to warm to ambient temperature overnight. After this time, the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×100 mL). The organic layers were washed with brine (50 mL), dried over sodium sulfate, and filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by chromatography (silica, heptane to 2:3 ethyl acetate/heptane) to afford 1-(4-nitrophenyl)-1,2-dihydro-3H-imidazo[1,2-a]benzimidazol-3-one (92 mg) as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe organic layers were washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by chromatography (silica, heptane to 2:3 ethyl acetate/heptane)

Sources & evidence

ORD record
ord-791a71407cf441d0aafef1f4825f588f
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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