Thionyl Chloride → HCID 86652112, compound

HRID 1895832Notes

Reaction equation

HRID 1895832 reaction equation
S(Cl)([Cl:3])=O.[Cl-:5].[CH2:6]([NH+:8]([CH2:15][CH3:16])[CH2:9][CH2:10][NH2+:11][CH2:12][CH2:13]O)[CH3:7].[Cl-]>ClCCl>[Cl-:3].[Cl:5][CH2:13][CH2:12][NH2+:11][CH2:10][CH2:9][NH+:8]([CH2:15][CH3:16])[CH2:6][CH3:7].[Cl-:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86652114HCID 86652114, compound

Product 1

HCID 86652112HCID 86652112, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of thionyl chloride (SOCl2) (16.9 g, 0.14 mol) in dichloromethane (20 ml) was added dropwise to a vigorously stirred suspension of N1,N1-diethyl-N2-(2-hydroxyethyl)ethane-1,2-diaminium chloride (21 g, 0.11 mol) in dichloromethane (120 ml) which was cooled at 0° C. The ice bath was removed and the reaction mixture was allowed to stir at room temperature for 1 hour. The mixture was then allowed to reflux for 1 hour. After cooling, the suspension was filtered and the product was washed with dichloromethane (40 ml) to give a colorless solid. (20 g, 78%). 1H NMR (methanol-d4): δ 4.03 (t, 3JHH=6.1, 2H, CH2Cl), 3.68 (br s, 4 H, CH2NH), 3.61 (t, 3JHH=5.7, 2H, Et2NCH2), 3.38 (q, 3JHH=7.3, 4H, CH3CH2), 1.43 (t, 3JHH=7.3, 6H, CH3).

Workup

  1. customThe ice bath was removed
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe suspension was filtered
  5. washthe product was washed with dichloromethane (40 ml)
  6. customto give a colorless solid

Sources & evidence

ORD record
ord-a0ef65f841c1474496696572b723ca57
Source dataset
uspto-grants-2013_08
Patent number
US08518368B2

Reaction notes

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