Formic Acid → HCID 20397149, compound

HRID 462766Notes

Reaction equation

HRID 462766 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[NH2:11][C:12]1[C:17]([Cl:18])=[CH:16][C:15]([NH:19][C:20](=[O:25])[C:21]([Cl:24])([Cl:23])[Cl:22])=[CH:14][C:13]=1[Cl:26]>>[Cl:26][C:13]1[CH:14]=[C:15]([NH:19][C:20](=[O:25])[C:21]([Cl:24])([Cl:22])[Cl:23])[CH:16]=[C:17]([Cl:18])[C:12]=1[NH:11][CH:1]=[O:3]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 20397151HCID 20397151, compound

Product 1

HCID 20397149HCID 20397149, compoundYield 69.1%

Conditions

Temperature
5 °C

Procedure

Acetic anhydride (600 mL, 6.4 mol) and 90% formic acid (275 mL, 5.4 mol) are heated to reflux for 45 minutes and then cooled to 5° C. The N-(4-amino-3,5-dichlorophenyl)-trichloroacetamide (464 g., 1.44 mol) is added to the mixed anhydride solution and mechanically stirred for 20 hours at room temperature. Then the reaction mixture is poured onto ice (2 liters). When the stirred slurry reaches room temperature, it is collected by suction filtration and washed with water (1.5 liters) and dried to constant weight yielding 348.7 grams of N-(3,5-dichloro-4-formamidophenyl)-trichloroacetamide with a mass spectral analysis of m/e+· 348 for C9H5Cl5N2O2.

Workup

  1. temperatureto reflux for 45 minutes
  2. additionThen the reaction mixture is poured onto ice (2 liters)
  3. customreaches room temperature
  4. filtrationit is collected by suction filtration
  5. washwashed with water (1.5 liters)
  6. customdried to constant weight

Sources & evidence

ORD record
ord-2aac8e9319aa4392b616a208045e4d8b
Source dataset
uspto-grants-1985_05
Patent number
US04517199

Reaction notes

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