Dimethylacetamide → HCID 59129370, compound

HRID 1908505Notes

Reaction equation

HRID 1908505 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])([CH3:4])([CH3:3])[CH3:2].C(C1C=CC([N+]([O-])=O)=C(C)C=1[N+]([O-])=O)(C)(C)C.C[C:36]([N:38]([CH3:40])[CH3:39])=O>CN(C=O)C>[C:1]([C:5]1[C:6]([N+:15]([O-:17])=[O:16])=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[C:9](/[CH:11]=[CH:36]/[N:38]([CH3:40])[CH3:39])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 533645731-Tert-butyl-5-methyl-2,4-dinitrobenzeneHCID 591294471-Tert-butyl-3-methyl-2,4-dinitrobenzene

Product 1

HCID 59129370HCID 59129370, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-tert-butyl-5-methyl-2,4-dinitrobenzene and 1-tert-butyl-3-methyl-2,4-dinitrobenzene (9.0 g, 38 mmol, 2:1 by NMR) and DMA (5.4 g, 45 mmol) in DMF (50 mL) was heated at reflux for 2 h before being cooled to room temperature. The reaction mixture was poured into water-ice and extracted with EtOAc (50 mL×3). The combined organic layers were washed with water and brine, before being evaporated to give a brown oil, which was purified by column to give (E)-2-(5-tert-butyl-2,4-dinitrophenyl)-N,N-dimethylethen-amine (5.0 g, 68%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. extractionextracted with EtOAc (50 mL×3)
  4. washThe combined organic layers were washed with water and brine
  5. custombefore being evaporated
  6. customto give a brown oil, which
  7. customwas purified by column

Sources & evidence

ORD record
ord-be62a75cefe949b595f2f9ffd1947633
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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