Water → HCID 58058402, compound

HRID 2041820Notes

Reaction equation

HRID 2041820 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-96eff56d55f447a4ab814224f0b8bff2
Source dataset
uspto-grants-2013_11
Patent number
US08586205B2

Reaction notes

Loading…