Methyl iodide → Ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]propionate

HRID 1164112Notes

Reaction equation

HRID 1164112 reaction equation
[H-].[Na+].[C:3]([CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[C:12]=1[O:25][CH3:26])[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4].[CH3:27]I>CN(C)C=O>[C:3]([C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[C:12]=1[O:25][CH3:26])([CH3:27])[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20513407Ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]acetate

Product 1

HCID 20513434Ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]propionateYield 102.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (65%, 1.05 g), ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]acetate (9.4 g), methyl iodide (7.85 g) and dimethylformamide (40 ml) were treated in a similar manner to that of Example 22-(2) to give oily ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]propionate (10.0 g).

Sources & evidence

ORD record
ord-a3b31626fd894283bcd4236533f034d9
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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