(Z)-N-(3-(3,4-dichlorophenyl)propyl)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-ylidene)acetamide → (Z)-N-((E)-4-(3,4-dichlorophenyl)but-3-enyl)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-ylidene)acetamide

HRID 1848394Notes

Reaction equation

HRID 1848394 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:23])/[CH:14]=[C:15]2\[O:16][C:17]([CH3:22])([CH3:21])[O:18][C:19]\2=[O:20])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[C:25]1C=C(/C=C/CCN)C=CC=1Cl>>[Cl:8][C:7]1[CH:6]=[C:5](/[CH:4]=[CH:9]/[CH2:10][CH2:11][NH:12][C:13](=[O:23])/[CH:14]=[C:15]2\[O:16][C:17]([CH3:21])([CH3:22])[O:18][C:19]\2=[O:20])[CH:25]=[CH:3][C:2]=1[Cl:1]

Participants

3

Reactant 2

HCID 21947512(Z)-N-(3-(3,4-dichlorophenyl)propyl)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-ylidene)acetamideHCID 63969265(E)-4-(3,4-dichlorophenyl)but-3-en-1-amine

Product 1

HCID 89477795(Z)-N-((E)-4-(3,4-dichlorophenyl)but-3-enyl)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-ylidene)acetamideYield 54%

Procedure

By appropriate application of method used to synthesize Intermediate 5, Intermediate 6 (41 mg, 0.19 mmol) was converted to Example 143 A (38 mg, 0.10 mmol, 54% yield). HPLC/MS (Method D) RT=1.06 min, [M+H]+ 370.

Sources & evidence

ORD record
ord-7d9d68b6ff9d4b53820b78a1471dd53f
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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