Dichloromethane → HCID 21487938, compound

HRID 1414608Notes

Reaction equation

HRID 1414608 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C(Cl)Cl.[CH2:15]([N:17]([CH2:37][CH3:38])[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[O:29][C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[CH:32]=2)=[CH:24][CH:23]=1)[CH3:16]>O>[C:1]([C:32]1[C:31]2[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=2[O:29][C:28]=1[C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:15][CH3:16])[CH2:37][CH3:38])=[CH:23][CH:24]=1)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7477p-Anisoyl chlorideHCID 10064795HCID 10064795, compound

Product 1

HCID 21487938HCID 21487938, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1.02 g. (0.006 mol.) of p-anisoyl chloride in 75 ml. of methylene chloride was added 2.0 g. (6.2 mmol.) of the hydrochloride salt of 2-[4'-(3-diethylaminopropoxy)phenyl]benzofuran. The reaction mixture was cooled to 0°, 3.3 ml. (0.024 mol.) of stannic chloride was added and the resulting mixture was stirred for 10 minutes at 0° then for 2.75 hours at 25°. The mixture was then poured into water and stirred vigorously. The layers were separated and the organic phase was washed with 10% aqueous sodium carbonate solution and water, dried (MgSO4) and concentrated to give the title compound as an oil.

Workup

  1. temperatureThe reaction mixture was cooled to 0°
  2. waitfor 2.75 hours at 25°
  3. stirringstirred vigorously
  4. customThe layers were separated
  5. washthe organic phase was washed with 10% aqueous sodium carbonate solution and water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-81fe2ac070c047a7a1505c33beba907d
Source dataset
uspto-grants-1977_01
Patent number
US04001426

Reaction notes

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