Water → 6-Bromo-N,N-diethylhexanamide

HRID 1586978Notes

Reaction equation

HRID 1586978 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[CH2:10]([NH:12][CH2:13][CH3:14])[CH3:11].O>O1CCCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([N:12]([CH2:13][CH3:14])[CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 8021DiethylamineHCID 898486-Bromohexanoyl chloride

Product 1

HCID 106582956-Bromo-N,N-diethylhexanamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-bromohexanoyl chloride (100 g, 468 mmol) in 350 ml of tetrahydrofuran was poured into a solution of diethylamine (1.08 moles, 79 g, 112 ml) in 800 ml of rapidly stirring water. The mixture was then extracted with 2×200 ml of CH2Cl2 and the pooled extracts were washed with 250 ml of brine. Drying over Na2SO4 and concentration under recuced pressure afforded 111.6 g (446 mmol, 100% yield) of product as a pale yellow oil: 1H NMR (Me2SO-d6, 300 MHz) δ3.5 (t, J=6.7 Hz, 2H), 3.2-3.3 (m, 4H), 2.3 (t, J=7.5 Hz, 2H), 1.8 (m, 2H), 1.3-1.6 (m, 4H), 1.1 (t, J=7.1 Hz, 3H), 0.99 (t, J=7.0 Hz, 3H).

Workup

  1. extractionThe mixture was then extracted with 2×200 ml of CH2Cl2
  2. washthe pooled extracts were washed with 250 ml of brine
  3. dry with materialDrying over Na2SO4 and concentration under recuced pressure

Sources & evidence

ORD record
ord-9118af7320394c9690479c2411d9e37c
Source dataset
uspto-grants-1993_06
Patent number
US05216165

Reaction notes

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