Nitrobenzene → HCID 21488051, compound

HRID 1414609Notes

Reaction equation

HRID 1414609 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[CH:18]=2)=[CH:10][CH:9]=1)[CH3:2].[N+](C1C=CC=CC=1)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:38][C:39]1[CH:40]=[C:41]([CH:45]=[C:46]([CH3:48])[CH:47]=1)[C:42](Cl)=[O:43]>O>[CH2:23]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[C:18]=2[C:42](=[O:43])[C:41]2[CH:45]=[C:46]([CH3:48])[CH:47]=[C:39]([CH3:38])[CH:40]=2)=[CH:12][CH:13]=1)[CH3:24]

Participants

6

Reactant 4

HCID 7416Nitrobenzene2×HCID 810883,5-Dimethylbenzoyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 10064795HCID 10064795, compound

Product 1

HCID 21488051HCID 21488051, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 2.0 g. (6.2 mmol.) of the hydrochloride salt of 2-[4'-(3-diethylaminopropoxy)phenyl]benzofuran in 10 ml. of nitrobenzene was added a solution of 1.84 g. (13.9 mmol.) of aluminum chloride in 20 ml. of nitrobenzene. The solution was cooled to 0° and 1.24 g. (7.4 mmol.) of 3,5-dimethylbenzoyl chloride was added. The reaction mixture was stirred at 0° for 30 minutes then at 25° for 1.5 hours, after which time it was poured into water and the nitrobenzene was removed by steam distillation. The aqueous solution was extracted with ether, made alkaline with aqueous sodium carbonate solution and again extracted with ether. The etheral solution was dried (MgSO4) and concentrated to give the title compound.

Workup

  1. additionTo a suspension of 2.0 g
  2. temperatureThe solution was cooled to 0°
  3. waitat 25° for 1.5 hours
  4. customthe nitrobenzene was removed by steam distillation
  5. extractionThe aqueous solution was extracted with ether
  6. extractionagain extracted with ether
  7. dry with materialThe etheral solution was dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cf6f5b20965a4b9f86f661f5153155df
Source dataset
uspto-grants-1977_01
Patent number
US04001426

Reaction notes

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