Acetone → HCID 11334362, compound

HRID 1182035Notes

Reaction equation

HRID 1182035 reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH3:7][C:8]1([CH3:16])[C:10]([CH3:12])([CH3:11])[CH:9]1[C:13]([OH:15])=O.[CH3:17][N:18]1[CH:22]=[CH:21][N:20]=[C:19]1[CH3:23].CC(C)=O>ClCCl>[Cl-:4].[CH3:23][C:19]1[N:20]([C:13]([CH:9]2[C:10]([CH3:11])([CH3:12])[C:8]2([CH3:7])[CH3:16])=[O:15])[CH:21]=[CH:22][N+:18]=1[CH3:17]

Participants

6

Reactant 4

HCID 180AcetoneHCID 156171,2-DimethylimidazoleHCID 65578Oxalyl chlorideHCID 1521152,2,3,3-Tetramethylcyclopropanecarboxylic acid

Product 1

HCID 11334362HCID 11334362, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

Oxalyl chloride (360 ml, 4.1 mol) was added over 65 min to a stirred solution of 2,2,3,3-tetramethylcyclopropane carboxylic acid (600 g, 4.2 mol) in dichloromethane (3.6 L) at 34° C. The solution was then heated to reflux for 30 min and then cooled to 5° C. A solution of 1,2-dimethylimidazole (490 g, 5.1 mol) in dichloromethane (1.2 L) was added over 45 min maintaining the internal temperature around 5° C. The resulting suspension was then warmed to 18° C. and acetone (4.8 L) was added over 45 minutes maintaining the internal temperature around 18° C. The slurry was cooled to 5° C. over 30 minutes, stirred at 5° C. for 30 minutes and then filtered. The product was colected by filtration, washed with acetone:dichloromethane (3:1, 3×1.2 L), sucked dry and then dried in a vacuum oven at 25-30° C. for 10 hours to give Intermediate 25 as a white solid (890 g) 1H nmr: δH (CDCl3, 400 MHz) 8.45 (d, J 2.4 Hz, 1H), 8.11 (d, J 2.4 Hz, 1H), 4.21 (s, 3H), 2.96 (s, 3H), 2.21 (s, 1H), 1.43 (s, 6H), 1.33 (s, 6H).

Workup

  1. temperatureThe solution was then heated
  2. temperatureto reflux for 30 min
  3. temperaturemaintaining the internal temperature around 5° C
  4. temperatureThe resulting suspension was then warmed to 18° C.
  5. temperaturemaintaining the internal temperature around 18° C
  6. temperatureThe slurry was cooled to 5° C. over 30 minutes
  7. filtrationfiltered
  8. filtrationThe product was colected by filtration
  9. washwashed with acetone:dichloromethane (3:1, 3×1.2 L)
  10. customsucked dry
  11. customdried in a vacuum oven at 25-30° C. for 10 hours

Sources & evidence

ORD record
ord-b814a53bd79e4d7483c409ff8ea9d578
Source dataset
uspto-grants-2007_10
Patent number
US07288536B2

Reaction notes

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