Water → N,N'-dimethoxy-N,N'-dimethylbutanediamide

HRID 490799

Reaction equation

HRID 490799 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][C:4](Cl)=[O:5].Cl.[CH3:10][NH:11][O:12][CH3:13].[N:14]1C=CC=C[CH:15]=1.[OH2:20].Cl[CH2:22]Cl>>[CH3:22][O:20][N:14]([CH3:15])[C:1](=[O:7])[CH2:2][CH2:3][C:4]([N:11]([O:12][CH3:13])[CH3:10])=[O:5]

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 6344DichloromethaneHCID 10970Succinyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 4379853N,N'-dimethoxy-N,N'-dimethylbutanediamide

Procedure

Dissolve 136.2 g of succinyl dichloride and 180.0 g N,O-dimethylhydroxylamine hydrochloride in 1.2 L dichloromethane and cool it in an ice bath. Add 305.9 g pyridine from an addition funnel with stir over 1.5 hours. Let the reaction mixture warm up to room temperature over night. Pour the reaction mixture into ice and water and separate the layers. Wash the organic layer with cold 2 N HCl (2×), water, 5% NaHCO3 (2×), and saturated brine. Dry over anhydrous Na2SO4 and evaporate to give crude product. It was washed with 3:1 hexanes and dichloromethane and dried to give the title compound as a light tan solid 1H NMR (CDCl3, 500 MHz δ: 3.70 (s, 6H), 3.15 (s, 6H), 2.74 (s, 4H).

Workup

  1. temperaturecool it in an ice bath
  2. customseparate the layers
  3. washWash the organic layer with cold 2 N HCl (2×), water, 5% NaHCO3 (2×), and saturated brine
  4. dry with materialDry over anhydrous Na2SO4
  5. customevaporate
  6. customto give crude product
  7. washIt was washed with 3:1 hexanes and dichloromethane
  8. customdried

Sources & evidence

ORD record
ord-7fe6b6bc418f4397a56f52d339a64eeb
Source dataset
uspto-grants-2009_05
Patent number
US07528163B2

Linked notes

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