Triethylamine → HCID 22715005, compound

HRID 352006Notes

Reaction equation

HRID 352006 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13](Cl)[C:12]([CH3:19])=[C:11]([CH3:20])[N:10]=1.[OH:21][C:22]([CH3:26])([CH3:25])[CH2:23][NH2:24]>CN(C)C=O>[Cl:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:24][CH2:23][C:22]([CH3:26])([OH:21])[CH3:25])[C:12]([CH3:19])=[C:11]([CH3:20])[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 951022-Propanol, 1-amino-2-methyl-HCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

Product 1

HCID 22715005HCID 22715005, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

Triethylamine (15.20 ml) was added to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (16.080 g) in dimethylformamide (160 ml), and then 2-hydroxy-2-methylpropylamine (7.143 g) was added with stirring. After 1 day the resulting mixture was cooled to about 5° C. After 4 days the solvent was removed under reduced pressure, and the resulting oil was dissolved in ethyl acetate (200 ml). The resulting solution was extracted with water (3×65 ml), and the combined aqueous layers were extracted with ethyl acetate (50 ml). The combined organic layers were dried with magnesium sulfate, and the solvent was removed under reduced pressure. The crystals that formed upon cooling were recrystallized from 1:1 hexane/ethyl acetate and then from ethyl acetate. The resulting purified crystals were used in the next step.

Workup

  1. customAfter 4 days the solvent was removed under reduced pressure
  2. dissolutionthe resulting oil was dissolved in ethyl acetate (200 ml)
  3. extractionThe resulting solution was extracted with water (3×65 ml)
  4. extractionthe combined aqueous layers were extracted with ethyl acetate (50 ml)
  5. dry with materialThe combined organic layers were dried with magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe crystals that formed
  8. temperatureupon cooling
  9. customwere recrystallized from 1:1 hexane/ethyl acetate
  10. customThe resulting purified crystals

Sources & evidence

ORD record
ord-35d9dcdf82ba45729414c3feb90cba06
Source dataset
uspto-grants-2004_06
Patent number
US06743920B2

Reaction notes

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