Water → HCID 3783248, compound

HRID 2114912Notes

Reaction equation

HRID 2114912 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](Cl)=[O:8].[F:10][C:11]([F:23])([F:22])[C:12]1[CH:21]=[CH:20][C:15]([C:16](=[N:18]O)[NH2:17])=[CH:14][CH:13]=1.O>O1CCOCC1>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[O:8][N:18]=[C:16]([C:15]2[CH:14]=[CH:13][C:12]([C:11]([F:10])([F:22])[F:23])=[CH:21][CH:20]=2)[N:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 609329N'-Hydroxy-4-(trifluoromethyl)benzene-1-carboximidamideHCID 27358243-Chlorothiophene-2-carbonyl chloride

Product 1

HCID 3783248HCID 3783248, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-chloro-thiophene-2-carbonyl chloride (455 mg, 2.51 mmol) and 4-trifluoromethyl-benzamidoxime (513 mg, 2.51 mmol) in 1,4-dioxane (50 mL) was refluxed for 1 h, then BF3OEt2 (0.1 mL) was added dropwise. The solution was refluxed for 5 h and cooled to room temperature. To the stirred solution was added water (100 mL) to produce precipitates. The solid was collected by filtration, washed with dioxane:water (1:1), and dried to yield 687 mg (82%) of the title compound. 1H NMR (CDCl3): 8.29 (d, J=8.1 Hz, 2H), 7.78 (d, J=8.4 Hz, 2H), 7.63 (d, J=5.1 Hz, 1H), 7.15 (d, J=5.1 Hz, 1H).

Workup

  1. additionBF3OEt2 (0.1 mL) was added dropwise
  2. temperatureThe solution was refluxed for 5 h
  3. customto produce
  4. customprecipitates
  5. filtrationThe solid was collected by filtration
  6. washwashed with dioxane:water (1:1)
  7. customdried

Sources & evidence

ORD record
ord-68189c3a4f464fde8644839492eb4cae
Source dataset
uspto-grants-2008_10
Patent number
US07435750B2

Reaction notes

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