Diethylaminoethyl chloride → 3-[4-(2-Diethylaminoethoxy)benzoyl]-2-(3,5-dimethylphenyl)benzofuran

HRID 2398468Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[O:10][C:11]3[CH:26]=[CH:25][CH:24]=[CH:23][C:12]=3[C:13]=2[C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31]Cl)[CH3:28].C1(C2OC3C=CC=CC=3C=2C(=O)C2C=CC(O)=CC=2)C=CC=CC=1.C(N(CC)CCCCl)C>>[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([C:13]2[C:12]3[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=3[O:10][C:9]=2[C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)=[O:22])=[CH:20][CH:19]=1)[CH3:28]

Participants

Reactant 4

HCID 13364Diethylaminoethyl chloride

HCID 669183-Chloropropyl(diethyl)amine

HCID 13264991(4-Hydroxyphenyl)(2-phenyl-1-benzofuran-3-yl)methanone

HCID 214353882-(3,5-Dimethylphenyl)-3-(4-hydroxybenzoyl)benzofuran

Product 1

HCID 214352653-[4-(2-Diethylaminoethoxy)benzoyl]-2-(3,5-dimethylphenyl)benzofuran

Procedure

Reaction of 2-(3,5-dimethylphenyl)-3-(4-hydroxybenzoyl)benzofuran with 2-diethylaminoethyl chloride by the procedure described in Example 1 for 2-phenyl-3-(4-hydroxybenzoyl)benzofuran and 3-diethylaminopropyl chloride gives 3-[4-(2-diethylaminoethoxy)benzoyl]-2-(3,5-dimethylphenyl)benzofuran.

Sources & evidence

ORD record: ord-4061f43f8fdd488697d4af4bc3d75fa2
Source dataset: uspto-grants-1977_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04024273

Reaction notes

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