Dimethylcarbamoyl Chloride → 3-(1-(4-((4-Ethoxyphenyl)ethynyl)phenyl)ethyl)-1,1-dimethylurea

HRID 76186Notes

Reaction equation

HRID 76186 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([NH2:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:2].[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]([NH:20][C:23](=[O:24])[N:22]([CH3:26])[CH3:21])[CH3:19])=[CH:16][CH:17]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 666103261-(4-((4-Ethoxyphenyl)ethynyl)phenyl)ethanamine

Product 1

HCID 569249903-(1-(4-((4-Ethoxyphenyl)ethynyl)phenyl)ethyl)-1,1-dimethylurea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 26.5 mg (0.10 mmol) 1-(4-((4-ethoxyphenyl)ethynyl)phenyl)ethanamine (I63) and 27.7 μL (0.20 mmol) TEA in 1.5 mL DCM are added 11.0 μl (0.12 mmol) dimethylcarbamyl chloride at 0° C. The reaction mixture is stirred at r.t. over night and directly purified by HPLC (MeOH/H2O/NH3).

Workup

  1. customdirectly purified by HPLC (MeOH/H2O/NH3)

Sources & evidence

ORD record
ord-0343594e86c4472581e234896a7c6929
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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