Water → 3-azido-N,N-diethyl-3-methylbutanamide

HRID 2061069Notes

Reaction equation

HRID 2061069 reaction equation
[N:1]([C:4]([CH3:10])([CH3:9])[CH2:5][C:6](Cl)=[O:7])=[N+:2]=[N-:3].[CH2:11]([NH:13][CH2:14][CH3:15])[CH3:12].O>ClCCCl>[N:1]([C:4]([CH3:10])([CH3:9])[CH2:5][C:6]([N:13]([CH2:14][CH3:15])[CH2:11][CH3:12])=[O:7])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 8021DiethylamineHCID 601345073-Azido-3-methylbutanoyl chloride

Product 1

HCID 601345763-azido-N,N-diethyl-3-methylbutanamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred ice cold solution of 3-azido-3-methylbutanoyl chloride (8.00 g, 49.5 mmol) in anhydrous DCE (160 mL) was added diethylamine (15.4 mL, 3 equiv, 0.148 mol) in one portion. The reaction was left to stir at 0° C. for 1 h. Water (200 mL) was added to the reaction mixture and the contents poured into a separatory funnel. The organic layer was separated and washed with water (3×100 mL) and brine (100 mL). It was dried over anhydrous MgSO4, filtered, concentrated and dried under high vacuum to give a crude oil (9.80 g, quant). This material was used without further purification.

Workup

  1. waitThe reaction was left
  2. additionthe contents poured into a separatory funnel
  3. customThe organic layer was separated
  4. washwashed with water (3×100 mL) and brine (100 mL)
  5. dry with materialIt was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried under high vacuum
  9. customto give a crude oil (9.80 g, quant)
  10. customThis material was used without further purification

Sources & evidence

ORD record
ord-15cf0ef959554a6aafa3bec6f2da8031
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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