Formic Acid → HCID 15172249, compound

HRID 1195598Notes

Reaction equation

HRID 1195598 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[C:11]([NH:15][C:16]([NH:18][O:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[Cl:27])=[O:17])([CH3:14])([CH3:13])[CH3:12]>C(OCC)(=O)C>[C:11]([NH:15][C:16]([N:18]([O:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[Cl:27])[CH:1]=[O:2])=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 13746399HCID 13746399, compound

Product 1

HCID 15172249HCID 15172249, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.53 g (33.3 mmoles) of formic acid and 3.24 g (31.8 mmoles) of acetic anhydride was stirred at 60° C. for 2.5 hours, and 2.20 g (7.94 mmoles) of 1-t-butyl-3-(2,5-dichlorophenoxy)urea was added. The mixture was stirred at 60° C. for 5 hours. The reaction mixture was cooled to room temperature, and 100 ml of ethyl acetate was added The mixture was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The ethyl acetate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane) to give 1.48 g of the desired compound as colorless crystals(yield 61 %).

Workup

  1. stirringThe mixture was stirred at 60° C. for 5 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwas washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe ethyl acetate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7244db25b7a24680aff7286102afe540
Source dataset
uspto-grants-1992_05
Patent number
US05112385

Reaction notes

Loading…