Carbon Dioxide → HCID 22238800, compound

HRID 1373365Notes

Reaction equation

HRID 1373365 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)(O)[O-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].[C:24](Cl)(=O)[CH2:25][CH:26]([CH3:28])[CH3:27].C(=O)=O>C1COCC1>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:6])[O:5][C:24]([CH2:25][CH:26]([CH3:28])[CH3:27])=[N:1][C:2]=2[CH:10]=1

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 24436Sodium SulfateHCID 66054Isovaleryl chlorideHCID 666462-Amino-4-chlorobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 22238800HCID 22238800, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A dry 3-necked, round bottomed flask, equipped with an overhead stirrer, thermometer, dropping funnel, cooling bath and condenser was charged with 406.41 g of 2-amino-4-chlorobenzoic acid (1 eq.), 270 g (1.35 eq.) of sodium bicarbonate, Na2SO4 (as a dehydrating agent) and 1,000 mL of THF. After commencing agitation, 354.7 g (1.2 eq.) of isovaleryl chloride was added dropwise. The reaction was exothermic and generated a gas (CO2). Temperature was maintained around 20–30° C. and completion of the reaction monitored by TLC (EtOAc/hexanes 1:1). The reaction mixture was then filtered and washed with THF (1,000 mL) the majority of which was then stripped off under vacuum. Acetic anhydride (1,450 mL) was then added to the reaction vessel and the temperature raised to 90–100° C. Completion of the reaction monitored by TLC (EtOAc/hexanes 1:1). The acetic anhydride was removed under vacuum at 80–100° C., followed by cooling to 60° C. The reaction vessel was then charged with heptane (1,000 mL) and cooled to 0° C. with stirring. The resulting precipitate was isolated by filtration and then washed with heptane (300 mL) and dried in a vacuum oven at 30° C. overnight to afford the title product (507 g, 90% yield).

Workup

  1. customA dry 3-necked, round bottomed flask, equipped with an overhead stirrer
  2. temperaturecooling bath and condenser
  3. additionwas added dropwise
  4. temperatureTemperature was maintained around 20–30° C.
  5. filtrationThe reaction mixture was then filtered
  6. washwashed with THF (1,000 mL) the majority of which
  7. additionAcetic anhydride (1,450 mL) was then added to the reaction vessel
  8. temperaturethe temperature raised to 90–100° C
  9. customThe acetic anhydride was removed under vacuum at 80–100° C.
  10. additionThe reaction vessel was then charged with heptane (1,000 mL)
  11. temperaturecooled to 0° C.
  12. customThe resulting precipitate was isolated by filtration
  13. washwashed with heptane (300 mL)
  14. customdried in a vacuum oven at 30° C. overnight

Sources & evidence

ORD record
ord-09871fd452584aa5888f8bccf5907983
Source dataset
uspto-grants-2007_01
Patent number
US07161002B2

Reaction notes

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