Chloroacetyl chloride → HCID 54074187, compound
Reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)[CH3:2].Cl[CH2:14][C:15](Cl)=[O:16]>C(Cl)(Cl)Cl>[CH2:11]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]2[C:15](=[O:16])[C:14](=[C:14]3[C:15](=[O:16])[C:7]4[CH:8]=[CH:9][C:4]([N:3]([CH2:1][CH3:2])[CH2:11][CH3:12])=[CH:5][C:6]=4[O:10]3)[O:10][C:6]=2[CH:5]=1)[CH3:12]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
1 g (6 mmol) of 3-diethylamino-phenol is dissolved is 20 ml of chloroform with exclusion of moisture. 1 g (9 mmol) of chloroacetyl chloride is added dropwise in the course of 30 minutes. Silica gel (about 10 g in total) is then introduced until the entire reaction solution has been absorbed, and the mixture is heated at 60-70° C. for 6 days. Finally, the silica gel is filtered off with suction through a G4 frit and washed with chloroform until the wash solution remains colourless. The dark red organic phases are combined and the solvent is stripped off on a rotary evaporator. 0.4 g of a dark red solid is obtained and is subsequently separated into the isomers by column chromatography over silica gel using chloroform as the solvent. The cis-isomer is obtained in the first runnings as a blue fraction, and the trans-isomer is obtained as a red-violet fraction. After the solvents have been stripped off, the resulting colorant isomers are dried at 95° C. under an oil pump vacuum for 7 hours.
Workup
- additionSilica gel (about 10 g in total) is then introduced until the entire reaction solution
- customhas been absorbed
- filtrationFinally, the silica gel is filtered off with suction through a G4 frit
- washwashed with chloroform until the wash solution
- customthe solvent is stripped off on a rotary evaporator
Sources & evidence
- ORD record
- ord-1cd29021ceea4a28ab915b48e648a7b2
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06156914
Reaction notes
Loading…