Dimethylacetamide → HCID 10614807, compound

HRID 1964365Notes

Reaction equation

HRID 1964365 reaction equation
[CH3:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]([C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C[C:20]([N:22]([CH3:24])[CH3:23])=O>CN(C=O)C>[CH3:20][N:22]([CH3:24])/[CH:23]=[CH:1]/[C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]([C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 31374DimethylacetamideHCID 15185318HCID 15185318, compound

Product 1

HCID 10614807HCID 10614807, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 3-methyl-2,6-dinitrobenzoate (35 g, 0.14 mol) and DMA (32 g, 0.27 mol) in DMF (200 mL) was heated at 100° C. for 5 h. The mixture was poured into ice water. The precipitated solid was filtered and washed with water to give (E)-ethyl 3-(2-(dimethylamino)vinyl)-2,6-dinitrobenzoate (25 g, 58%).

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-7d503459cee44d639d1267a5cbabde08
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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