Dimethylcarbamoyl Chloride → N,N-dimethyl-3-[4-(4-n-propyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)phenyl]-prop-2-ynthioamide

HRID 466525Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]23[O:16][CH2:15][C:12]([CH2:17][CH2:18][CH3:19])([CH2:13][O:14]2)[CH2:11][O:10]3)=[CH:5][CH:4]=1)#[CH:2].CN(C)C(Cl)=O.[CH3:26][N:27]([CH3:31])[C:28](Cl)=[S:29]>>[CH3:26][N:27]([CH3:31])[C:28](=[S:29])[C:2]#[C:1][C:3]1[CH:4]=[CH:5][C:6]([C:9]23[O:10][CH2:11][C:12]([CH2:17][CH2:18][CH3:19])([CH2:13][O:14]2)[CH2:15][O:16]3)=[CH:7][CH:8]=1

Participants

Reactant 3

HCID 6598Dimethylcarbamoyl Chloride

HCID 27871Dimethylthiocarbamoyl chloride

HCID 1152231-(4-Ethynylphenyl)-4-propyl-2,6,7-trioxabicyclo(2.2.2)octane

Product 1

HCID 15021992N,N-dimethyl-3-[4-(4-n-propyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)phenyl]-prop-2-ynthioamide

Procedure

N,N-Dimethyl-3-[4-(4-(4-n-propyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)phenyl]-prop-2-ynamide and N,N-dimethyl-3-[4-(4-n-propyl-2,6,7-trioxabicyclo[2,2,2]-oct-1-yl) phenyl]-prop-2-ynthioamide were prepared using similar methodology from 1-(4-ethynylphenyl)-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane and dimethylcarbamoyl chloride and dimethylthiocarbamoyl chloride respectively.

Sources & evidence

ORD record: ord-0608fc33820340f798eedd8d6a2dc325
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05157029

Reaction notes

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