Dimethylamine → HCID 18376807, compound

HRID 844153Notes

Reaction equation

HRID 844153 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12](Cl)[C:11]=2[N+:18]([O-:20])=[O:19])=[N:6][CH:7]=1.[CH3:22][NH:23][CH3:24].O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([N:23]([CH3:24])[CH3:22])[C:11]=2[N+:18]([O-:20])=[O:19])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 18376742HCID 18376742, compound

Product 1

HCID 18376807HCID 18376807, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

Into a solution of N-(5-chloropyridin-2-yl)-2-nitro-3,5-dichlorobenzamide (4.0 g, 12 mmol) in dimethyl sulfoxide (60 mL) was bubbled an excess of dimethyl amine gas. The mixture was sealed in a pressure tube and heated at 50° C. After 3 hours, the mixture was cooled to ambient temperature, then poured into water, and extracted with methylene chloride. The combined organic extracts were dried over MgSO4, and concentrated in vacuo to afford 3.8 g (93% yield) of N-(5-chloropyridin-2-yl)-2-nitro-3-dimethylamino-5-chlorobenzamide; NMR (CDCl3) 9.6 (s, 1), 8.2 (d, 1), 7.8 (d, 1), 7.7 (dd, 1), 7.1 (d, 1), 6.9 (d, 1), 2.8 (s, 6) ppm.

Workup

  1. customThe mixture was sealed in a pressure tube
  2. temperaturethe mixture was cooled to ambient temperature
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2320183d2eb0407f84f6af52b16e67b7
Source dataset
uspto-grants-2002_04
Patent number
US06380221B1

Reaction notes

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