Carbon Dioxide → HCID 21475509, compound

HRID 440619Notes

Reaction equation

HRID 440619 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

5

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 199777511191-27-1

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.

Workup

  1. customequipped with a reflux condenser
  2. customAs reaction
  3. additionAfter addition
  4. temperaturethe mixture is cooled to room temperature over 45 min
  5. customExcess oxalyl chloride is removed first by rotary evaporation at 50° C. (water aspirator vacuum)
  6. distillationby Kugelrohr distillation at 60° C. (0.3 mm Hg) for 3 h

Sources & evidence

ORD record
ord-1e1d38c615d940ce82dc5f522df2c864
Source dataset
uspto-grants-1996_05
Patent number
US05520835

Reaction notes

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