Carbon Dioxide → HCID 21475509, compound

Reaction equation

C(Cl)(=O)C([Cl:4])=O.[ClH:7].[CH3:8][N:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](O)=[O:17])[CH3:10].Cl.C(=O)=O>>[ClH:4].[CH3:8][N:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([Cl:7])=[O:17])[CH3:10]

Participants

Reactant 4

HCID 280Carbon Dioxide

HCID 313Hydrochloric Acid

HCID 65578Oxalyl chloride

HCID 199777516-(Dimethylamino)hexanoic acid hydrochloride

Product 1

HCID 21475509HCID 21475509, compound

Conditions

Temperature: 30 °C

Procedure

Oxalyl chloride (3367.33 g, 26.53 mol) is placed in a 5000 mL three-necked round-bottomed flask equipped with a reflux condenser, internal thermometer, mechanical stirrer, and argon inlet. 6-(N,N-Dimethylamino)hexanoic acidhydrochloride (1146.00 g, 5.86 mol) is added over 3 h while maintaining the reaction temperature between 25-35 ° C. As reaction takes place, HCl, CO2, and CO are swept away from the mixture with argon. After addition is complete, the mixture is cooled to room temperature over 45 min. Excess oxalyl chloride is removed first by rotary evaporation at 50° C. (water aspirator vacuum) and then by Kugelrohr distillation at 60° C. (0.3 mm Hg) for 3 h. A quantitative yield of 3 is isolated as a dark red oil that solidifies on standing.