Hydrochloric Acid → HCID 22921571, compound

HRID 2258621Notes

Reaction equation

HRID 2258621 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][C:7]=1[N:19]([C:28]([C:30]([F:33])([F:32])[F:31])=[O:29])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)=O.C(=O)([O-])[O-].[K+].[K+].O.Cl>CO>[F:32][C:30]([F:31])([F:33])[C:28]([N:19]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)[C:7]1[CH:8]=[C:9]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10]([F:12])=[CH:11][C:6]=1[NH2:5])=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 11430Potassium CarbonateHCID 22921577HCID 22921577, compound

Product 1

HCID 22921571HCID 22921571, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.7 grams (0.007 mole) of N-trifluoromethylcarbonyl-2-[(trifluoromethylcarbonyl)(3-chlorophenylmethyl)amino]-4-ethoxycarbonylamino-5-fluoroaniline in 50 mL of methanol was stirred, and a solution of 1.0 gram (0.007 mole) of potassium carbonate in a minimum amount of water was added. The reaction mixture was then heated at reflux for about three hours, after which the reaction mixture was cooled, poured into cold water, and acidified to a pH of 6 with aqueous 3N hydrochloric acid. The resultant solid was collected by filtration and dried, yielding 3.2 grams of 2-[(trifluoromethylcarbonyl)(3-chlorophenylmethyl)amino]-4-ethoxycarbonylamino-5-fluoroaniline. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for about three hours
  3. temperatureafter which the reaction mixture was cooled
  4. filtrationThe resultant solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-678124911c854b75a26bd161f7c4d700
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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