Thionyl Chloride → HCID 19915718, compound

HRID 1089695Notes

Reaction equation

HRID 1089695 reaction equation
[CH3:1][N:2]([CH2:14][CH2:15]O)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.S(Cl)([Cl:19])=O>C(Cl)Cl>[ClH:19].[CH3:1][N:2]([CH2:14][CH2:15][Cl:19])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19915726HCID 19915726, compound

Product 1

HCID 19915718HCID 19915718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[N-methyl-N-(4-nitrophenethyl)amino]ethanol (8.0 g) in dry methylene chloride (75 ml) was added dropwise thionyl chloride (3ml) with stirring at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 16 hours. The resultant solid was filtered, washed with dry ether and dried to give a colourless product (7.1 g). Crystallisation from ethyl acetate/methanol gave the title compound, 6.0 g, m.p. 168°-169°.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 16 hours
  3. filtrationThe resultant solid was filtered
  4. washwashed with dry ether
  5. customdried

Sources & evidence

ORD record
ord-356acab45d70431bbbcb455e0a8c0b26
Source dataset
uspto-grants-1992_01
Patent number
US05079248

Reaction notes

Loading…