Water → HCID 60134438, compound

HRID 2061046Notes

Reaction equation

HRID 2061046 reaction equation
[N:1]([C:4]([CH3:10])([CH3:9])[CH2:5][C:6](Cl)=[O:7])=[N+:2]=[N-:3].[CH2:11]([NH:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14].O>ClCCCl>[N:1]([C:4]([CH3:10])([CH3:9])[CH2:5][C:6]([N:15]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH2:12][CH2:13][CH3:14])=[O:7])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 8148DibutylamineHCID 601345073-Azido-3-methylbutanoyl chloride

Product 1

HCID 60134438HCID 60134438, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a stirred ice cold solution of 3-azido-3-methylbutanoyl chloride (10.0 g, 61.8 mmol) in anhydrous DCE (150 mL) was added dibutylamine (21.5 mL, 2 equiv, 0.123 mol) in one portion. A white solid formed immediately and the suspension was stirred vigorously for 3 h at room temperature. DCE (200 mL) and 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 (2×200 mL) and brine (200 mL). It was dried over anhydrous MgSO4, filtered, concentrated and dried under high vacuum to give a crude oil (15.7 g, quantitative). This material was used without further purification. 1H NMR (CDCl3, 400 MHz): δ 0.91-0.97 (dt, J=7.2, 7.4, 12H), 1.21-1.38 (m, 4H), 1.46 (s, 6H), 1.47-1.57 (m, 4H), 2.47 (s, 4H), 3.25-3.32 (m, 4H). LRMS (ESI+) for C13H26N4O (254.2); Found: 255 (MH+)

Workup

  1. customA white solid formed immediately
  2. additionthe contents poured into a separatory funnel
  3. customThe organic layer was separated
  4. washwashed with water (2×200 mL) and brine (200 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 (15.7 g, quantitative)
  10. customThis material was used without further purification

Sources & evidence

ORD record
ord-937d19e6e36c40a88ce8bb7bc7352191
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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