Toluene → HCID 15324180, compound

HRID 446565Notes

Reaction equation

HRID 446565 reaction equation
C1(C)C=CC=CC=1.Br.[Br:9][CH2:10][CH2:11][CH2:12][NH2:13].C(N(CC)CC)C.[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)([O-:23])=[O:22]>C(OCC)(=O)C>[Br:9][CH2:10][CH2:11][CH2:12][NH:13][C:28](=[O:29])[C:27]1[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 787013-Bromopropylamine hydrobromide

Product 1

HCID 15324180HCID 15324180, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

30 mL of toluene was added to 3-bromopropylamine hydrobromide (1.20 g, 5.50 mmol), and triethylamine (1.53 mL, 11.0 mmol) was added dropwise with stirring under ice cooling. After the dropwise addition was completed, 4-nitrobenzoyl chloride (928 mg, 5.50 mmol) was added little by little, and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with an aqueous saturated sodium hydrogencarbonate solution, a 0.1 N aqueous hydrochloric acid solution, and saturated sodium chloride solution. The organic layer was dried with anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to give the title compound (1.11 g; yield, 77%) as light yellow crystals.

Workup

  1. additionwas added dropwise
  2. additionAfter the dropwise addition
  3. stirringwas stirred at room temperature for 15 minutes
  4. washthe organic layer was washed with an aqueous saturated sodium hydrogencarbonate solution
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d78f2cf8a92c48d7bc8ae0396c9955b1
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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