Water → N-Ethyl-2,6-dimethylaniline

HRID 877853Notes

Reaction equation

HRID 877853 reaction equation
[BH4-].[Na+].[CH:3](=[N:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])[CH3:4].O>C1COCC1.CO>[CH2:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])[CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 10993945HCID 10993945, compound

Product 1

HCID 12539332N-Ethyl-2,6-dimethylaniline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (19.0 g, 0.5 mol) was added in small portions to a stirred solution of N-ethylidene-2,6-dimethylaniline (36.3 g, 0.247 mol) in THF (150 mL) and methanol (150 mL). The reaction was exothermic and a water/ice bath was used to cool the mixture. After addition of sodium borohydride, the bath was removed and the mixture was allowed to react for another 30 min. Then, water (150 mL) was added to the reaction mixture, while stirring and cooling the mixture with a water/ice bath. The volatiles were removed in vacuo, the aqueous layer extracted with dichloromethane (3×150 mL) and the combined organic layers were dried with sodium sulfate. Filtration and rotatory vaporation of the volatiles yielded the desired product. Yield: 36.4 g (99%).

Workup

  1. customa water/ice bath was used
  2. temperatureto cool the mixture
  3. customthe bath was removed
  4. customto react for another 30 min
  5. temperaturecooling the mixture with a water/ice bath
  6. customThe volatiles were removed in vacuo
  7. extractionthe aqueous layer extracted with dichloromethane (3×150 mL)
  8. dry with materialthe combined organic layers were dried with sodium sulfate
  9. filtrationFiltration and rotatory vaporation of the volatiles

Sources & evidence

ORD record
ord-7fcc7134915e4f7990d21e0ca7776db3
Source dataset
uspto-grants-2015_03
Patent number
US08987393B2

Reaction notes

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