Water → HCID 66939361, compound

HRID 1257422Notes

Reaction equation

HRID 1257422 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)[NH2:4].Cl[C:16](=O)[CH2:17][N:18]1[CH:22]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:20]=[N:19]1.O>N1C=CC=CC=1>[F:14][C:11]([F:13])([F:12])[C:7]1[CH:6]=[C:5]([C:3]2[N:4]=[C:16]([CH2:17][N:18]3[CH:22]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:20]=[N:19]3)[O:1][N:2]=2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 609330N'-hydroxy-3-(trifluoromethyl)benzimidamideHCID 58127969HCID 58127969, compound

Product 1

HCID 66939361HCID 66939361, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

A solution of N′-hydroxy-3-(trifluoromethyl)benzenecarboximidamide (2.1 g) in pyridine (20 mL) was cooled in an ice bath, and the compound (2.3 g) obtained in Example 115c was added. The reaction mixture was stirred overnight with heating at 110-120° C. The mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was separated, washed successively with 1N hydrochloric acid and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: petroleum ether-ethyl acetate) to give the title compound (0.38 g) as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe ethyl acetate layer was separated
  3. washwashed successively with 1N hydrochloric acid and saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (carrier: silica gel, eluent: petroleum ether-ethyl acetate)

Sources & evidence

ORD record
ord-bbb7264266f546f2b8552eebeb0808ec
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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