Trichloroacetyl chloride → HCID 18376776, compound

HRID 2300922Notes

Reaction equation

HRID 2300922 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:33])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([O:17][CH3:18])[C:11]=2[NH:19][C:20]([C:22]2[S:23][CH:24]=[C:25]([CH2:28][C:29]([NH2:32])=[N:30][OH:31])[C:26]=2[Cl:27])=[O:21])=[N:6][CH:7]=1.[Cl:34][C:35]([Cl:40])([Cl:39])[C:36](O)=O.ClC(Cl)(Cl)C(Cl)=O.[OH-].[Na+]>O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:33])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([O:17][CH3:18])[C:11]=2[NH:19][C:20]([C:22]2[S:23][CH:24]=[C:25]([CH2:28][C:29]3[N:32]=[C:36]([C:35]([Cl:40])([Cl:39])[Cl:34])[O:31][N:30]=3)[C:26]=2[Cl:27])=[O:21])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 6420Trichloroacetyl chlorideHCID 6421Trichloroacetic AcidHCID 14798Sodium HydroxideHCID 53960659HCID 53960659, compound

Product 1

HCID 18376776HCID 18376776, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

N-(5-Chloropyridin-2-yl)-2-[((4-(2-amino-2-(hydroxyimino)ethyl)-3-chlorothiophen-2-yl)carbonyl)amino]-3-methoxy-5-chlorobenzamide (3.06 g, 5.8 mmol) was dissolved in trichloroacetic acid (3.8 g, 23 mmol) and the mixture heated to 85° C. Trichloroacetyl chloride (1.3 mL, 11.6 mmol) was added, and the temperature was increased to 94° C. After one hour the reaction mixture was allowed to cool to room temperature, diluted with water (150 mL) and a small amount of ethyl acetate, and adjusted to basic pH with 1 N NaOH. The aqueous layer was extracted with ethyl acetate (300 mL). The organic phase was washed with 1 M sodium bicarbonate (150 mL), dried over magnesium sulfate, concentrated in vacuo, and dried under vacuum. The crude product was purified by flash chromatography on silica gel eluting with 25% ethyl acetate/hexanes to afford N-(5-chloropyridin-2-yl)-2-[((4-((5-trichloromethyl-1,2,4-oxadiazol-3-yl)methyl)-3-chlorothiophen-2-yl)carbonyl)amino]-3-methoxy-5-chlorobenzamide.

Workup

  1. temperaturethe temperature was increased to 94° C
  2. temperatureto cool to room temperature
  3. extractionThe aqueous layer was extracted with ethyl acetate (300 mL)
  4. washThe organic phase was washed with 1 M sodium bicarbonate (150 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customdried under vacuum
  8. customThe crude product was purified by flash chromatography on silica gel eluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f32084e4fb7741559c018f284308caa2
Source dataset
uspto-grants-2002_12
Patent number
US06498185B1

Reaction notes

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