Hydrochloric Acid → 3-(4'-Chlorobiphenyl-4-yl)propynoic acid-[3-chloro-4-(2-dimethylaminoethoxy)phenyl]amide hydrochloride

HRID 735055Notes

Reaction equation

HRID 735055 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]([OH:18])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22]([NH2:34])[CH:23]=[CH:24][C:25]=1[O:26][CH2:27][CH2:28][N:29]([CH2:32]C)[CH2:30]C.Cl.ClCl>ClCCl.CO>[ClH:1].[Cl:19][C:20]1[CH:21]=[C:22]([NH:34][C:16](=[O:18])[C:15]#[C:14][C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[CH:13][CH:12]=2)[CH:23]=[CH:24][C:25]=1[O:26][CH2:27][CH2:28][N:29]([CH3:30])[CH3:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24526Chlorine2×HCID 167916763-Chloro-4-(2-diethylaminoethoxy)phenylamineHCID 68816492(4'-Chlorobiphenyl-4-yl)propynoic acid

Product 1

HCID 688167723-(4'-Chlorobiphenyl-4-yl)propynoic acid-[3-chloro-4-(2-dimethylaminoethoxy)phenyl]amide hydrochloride

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 3.7.c. from (4′-chlorobiphenyl-4-yl)propynoic acid and 3-chloro-4-(2-diethylaminoethoxy)phenylamine. Yield: 0.28 g (58% of theory); melting point: 226° C.-233° C.; C27H26Cl2N2O2 (M=481.41)*HCl; calc.: molecular ion peak (M+H)+: 481/3/5 (Cl2); found: molecular ion peak (M+H)+: 481/3/5 (Cl2); Rf value: 0.45 (silica gel, dichloromethane/methanol (90:10)).

Workup

  1. customPrepared analogously to Example 3.7.c

Sources & evidence

ORD record
ord-361bfbbd443c479e9c122bdfae2f7ce2
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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