Dichloromethane → 3-[4-(2-Diethylaminoethoxy)benzoyl]-2-(4-methoxyphenyl)benzofuran

HRID 268350Notes

Reaction equation

HRID 268350 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[CH:13]=2)=[CH:5][CH:4]=1.Cl.[CH2:19]([N:21]([CH2:34][CH3:35])[CH2:22][CH2:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)[CH3:20].C(Cl)Cl>O>[CH2:34]([N:21]([CH2:19][CH3:20])[CH2:22][CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([C:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[O:10][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:30])=[CH:32][CH:33]=1)[CH3:35]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10727834HCID 10727834, compoundHCID 161118754-(2-Diethylaminoethoxy)benzoyl chloride hydrochloride

Product 1

HCID 214352803-[4-(2-Diethylaminoethoxy)benzoyl]-2-(4-methoxyphenyl)benzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 11.2 g. (0.05 mol.) of 2-(4-methoxyphenyl)benzofuran and 14.6 g. (0.05 mol.) of 4-(2-diethylaminoethoxy)benzoyl chloride hydrochloride in 100 ml. of methylene chloride is added 39.1 g. (0.15 mol.) of stannic chloride. The reaction mixture is stirred for 1.5 hours at ambient temperature then poured into water. The layers are separated and the organic phase is washed with aqueous sodium carbonate until basic and water, dried (MgSO4) and concentrated to give the title compound.

Workup

  1. additionTo a mixture of 11.2 g
  2. customThe layers are separated
  3. washthe organic phase is washed with aqueous sodium carbonate until basic and water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-964d94d2421c4b1392e6fa0c0ff9ad6d
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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