Tetrahydrofuran → HCID 53927404, compound

HRID 2412438Notes

Reaction equation

HRID 2412438 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[C:10]([C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH2:14])[CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[NH2:21])([CH3:3])[CH3:2].[Br:22]N1C(=O)CCC1=O.O1CCCC1>C(OCC)(=O)C>[CH:1]([N:4]1[C:8]2[CH:9]=[C:10]([C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:14][Br:22])[CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[NH2:21])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 20432649HCID 20432649, compound

Product 1

HCID 53927404HCID 53927404, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Three hundred milligrams (1.08 mmoles) of 1-isopropyl-2-amino-6-(1-phenylethenyl)benzimidazole and 192 mg. (1.08 mmoles) of N-bromosuccinimide were refluxed overnight in 20 ml. of dry tetrahydrofuran. After cooling, ethyl acetate was added and the solution was washed with a saturated solution of sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered, and evaporated in vacuo. The residue was chromatographed over silica gel, first eluting with ethyl acetate to remove impurities, and then with 10% methanol/90% ethyl acetate. The title product was crystallized from ether giving 200 mg. of the cis/trans mixture, M+ =357.

Workup

  1. temperatureAfter cooling
  2. washthe solution was washed with a saturated solution of sodium bicarbonate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was chromatographed over silica gel
  7. washfirst eluting with ethyl acetate
  8. customto remove impurities
  9. customThe title product was crystallized from ether giving 200 mg

Sources & evidence

ORD record
ord-cd5d68f4fb2642c5a2ef1b1942e85a42
Source dataset
uspto-grants-1985_01
Patent number
US04492708

Reaction notes

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