Dimethylamine → HCID 18980103, compound

HRID 2392668Notes

Reaction equation

HRID 2392668 reaction equation
Cl[CH2:2][C:3]([N:5]([CH3:17])[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[O:15][CH3:16])=[O:4].[CH3:18][NH:19][CH3:20]>C(O)C>[CH3:18][N:19]([CH3:20])[CH2:2][C:3]([N:5]([CH3:17])[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[O:15][CH3:16])=[O:4]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 14980494HCID 14980494, compound

Product 1

HCID 18980103HCID 18980103, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-2'-methoxy-N-methyl-5'-nitroacetanilide (D86) (1.01 g, 3.9 mmol) and dimethylamine (33% in IMS, 2 ml) were stirred in ethanol (10 ml) for 3 days. After evaporation to dryness in vacuo, the crude product was partitioned between 2M HCl and ethyl acetate. The aqueous portion was basified with potassium carbonate solution, and extracted with chloroform. The extract was dried (Na2SO4) and evaporated in vacuo to give the title compound as a dark oil (0.85 g, 81%).

Workup

  1. customAfter evaporation to dryness in vacuo
  2. customthe crude product was partitioned between 2M HCl and ethyl acetate
  3. extractionextracted with chloroform
  4. dry with materialThe extract was dried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-62895a888d714a8698514e58f4401559
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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