Dimethylformamide → HCID 20994726, compound

HRID 1486664Notes

Reaction equation

HRID 1486664 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(N([CH2:16][CH3:17])CC)C.[C:18](Cl)(=[O:22])[C:19](Cl)=[O:20].CN(C=[O:28])C>ClCCl>[O:20]=[C:19]([NH:10][NH:9][C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:8])[C:18]([O:22][CH2:16][CH3:17])=[O:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 11112Nicotinic acid, hydrazideHCID 65578Oxalyl chloride

Product 1

HCID 20994726HCID 20994726, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

28.0 g (204 mmol) of nicotinic hydrazide were dissolved in 700 ml of DMF by gentle heating, then 52.5 g (518 mmol) of triethylamine were added and, while cooling with an ice bath, a solution of 31.7 g (232 mmol) of oxalyl chloride in 40 ml of dichloromethane was added dropwise. The mixture was stirred for 15 minutes and concentrated by evaporation, and the residue was partitioned between water (pH7) and chloroform/isopropanol (10:1). The organic phase was dried and concentrated under reduced pressure.

Workup

  1. temperaturewhile cooling with an ice bath
  2. concentrationconcentrated by evaporation
  3. customthe residue was partitioned between water (pH7) and chloroform/isopropanol (10:1)
  4. customThe organic phase was dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ce9e20df3dc44b6b348113e9d38a27e
Source dataset
uspto-grants-2016_08
Patent number
US09428487B2

Reaction notes

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