1,1'-Carbonyldiimidazole → HCID 86703514, compound

HRID 1849651Notes

Reaction equation

HRID 1849651 reaction equation
[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:25]1([S:28]([NH2:31])(=[O:30])=[O:29])[CH2:27][CH2:26]1>C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:31][S:28]([CH:25]1[CH2:27][CH2:26]1)(=[O:30])=[O:29])=[O:9]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 148764175-Chloro-2,4-difluorobenzoic acidHCID 15765418Cyclopropanesulfonamide

Product 1

HCID 86703514HCID 86703514, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-chloro-2,4-difluorobenzoic acid (10.0 g, 51.93 mmol) and 1,1′-carbonyldiimidazole (10.11 g, 62.32 mmol) was stirred at reflux for 2 hours, cooled to ambient temperature, and cyclopropanesulfonamide (7.55 g, 62.32 mmol) was added. The reaction mixture was stirred at ambient temperature for 16 hours, diluted with ethyl acetate (300 mL), washed with 1M aqueous hydrochloric acid, brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was re-crystallized from ethyl acetate/hexanes mixture (1:2) to afford the title compound as a colorless solid (7.7 g, 56%): MS (ES−) m/z 294.1 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. stirringThe reaction mixture was stirred at ambient temperature for 16 hours
  3. washwashed with 1M aqueous hydrochloric acid, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was re-crystallized from ethyl acetate/hexanes mixture (1:2)

Sources & evidence

ORD record
ord-1cdd9d6402874230b44abd88364c15ba
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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