Thionyl Chloride → HCID 15105203, compound

HRID 1729066Notes

Reaction equation

HRID 1729066 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([N:7]([CH2:14][CH3:15])[CH2:8][CH2:9][O:10][CH2:11][CH2:12]O)[CH3:6]>C1C=CC=CC=1>[CH2:5]([N:7]([CH2:14][CH3:15])[CH2:8][CH2:9][O:10][CH2:11][CH2:12][Cl:3])[CH3:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 673272-[2-(Diethylamino)ethoxy]ethanol

Product 1

HCID 15105203HCID 15105203, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A modification of the procedure described in J. Am. Chem. Soc. 76:3163 (1954) was used to obtain this compound, beginning with the dropwise addition of thionyl chloride (17.02 mL, 233.42 mmol) to a solution of 2-(2-di-ethylaminoethoxy)-ethanol in benzene (100 mL). The reaction mixture was stirred at reflux for 1.5 hours and the volatiles were removedunder diminished pressure. The oily residue crystallized in ether, was nearly homogeneous by TLC, and was used without further purification. The HCl salt obtained in this reaction was very hygroscopic. Attempts at purification of the free base via distillation resulted in decomposition. CIMS 180 m/z (M+1), 183 m/z (M+3).

Workup

  1. customto obtain this compound
  2. temperatureat reflux for 1.5 hours
  3. customThe oily residue crystallized in ether
  4. customwas used without further purification

Sources & evidence

ORD record
ord-7c93661356254db29514a6f9d4a195ae
Source dataset
uspto-grants-1994_07
Patent number
US05331010

Reaction notes

Loading…