1,2-Dichloroethane → 2-Ethoxy-2-methylpropanamide

HRID 1049302Notes

Reaction equation

HRID 1049302 reaction equation
[CH2:1]([O:3][C:4]([CH3:9])([CH3:8])[C:5](O)=[O:6])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=[N:20]C=2C=1.[NH4+].[OH-]>CC#N>[CH2:1]([O:3][C:4]([CH3:9])([CH3:8])[C:5]([NH2:20])=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 144596782-Ethoxy-2-methylpropanoic acid

Product 1

HCID 904032482-Ethoxy-2-methylpropanamideYield 101%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-ethoxy-2-methylpropanoic acid (1.1 g, 8.32 mmol) in MeCN (15 mL) was treated with EDC (1.596 g, 8.32 mmol) and HOBT (1.275 g, 8.32 mmol), stirred at RT for 2 h, treated with NH4OH (˜15M, 1.7 mL, ˜25.5 mmol) and stirred at RT overnight. The mixture was treated with satd. NaHCO3 and water, extracted with EtOAc (5×) and the combined organics were dried over MgSO4 and concentrated to dryness to afford 2-ethoxy-2-methylpropanamide (1.1 g, 101%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 7.03 (s, 2H), 3.31 (q, J=7.0 Hz, 2H), 1.21 (s, 6H), 1.10 (t, J=7.0 Hz, 3H).

Workup

  1. stirringstirred at RT overnight
  2. additionThe mixture was treated with satd
  3. extractionNaHCO3 and water, extracted with EtOAc (5×)
  4. dry with materialthe combined organics were dried over MgSO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-01b1df89bdc44bb691b20844de6e3864
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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