Water → HCID 58058402, compound

HRID 2405622Notes

Reaction equation

HRID 2405622 reaction equation
[C:1]1([NH:7][C:8]2[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19].C(N(CC)CC)C.O>ClCCl>[Br:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([NH:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 235422-Bromobenzoyl chlorideHCID 68297N-Phenyl-o-phenylenediamine

Product 1

HCID 58058402HCID 58058402, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-phenylbenzene-1,2-diamine (6.08 g, 30 mmol) in anhydrous dichloromethane (˜100 mL), was added 2-bromobenzoylchloride (6.585 g, 33 mmol), followed by triethylamine (7.0 mL, 50 mmol) slowly with water bath cooling. After the additions, the whole was stirred at room temperature overnight. The resulting mixture was poured into water (˜150 mL) and extracted with dichloromethane (˜100 mL) twice. The organic phase was collected, dried over Na2SO4, concentrated and recrystallized in dichloromethane/hexanes to give a white solid (10.7 g, in 92% yield).

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane (˜100 mL) twice
  3. customThe organic phase was collected
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customrecrystallized in dichloromethane/hexanes
  7. customto give a white solid (10.7 g, in 92% yield)

Sources & evidence

ORD record
ord-ff07e729ba2145f48c217f29d25d9f6b
Source dataset
uspto-grants-2014_08
Patent number
US08808879B2

Reaction notes

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