Water → HCID 22147854, compound

HRID 2114914Notes

Reaction equation

HRID 2114914 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=O.S(Cl)(Cl)=O.[Cl:14][C:15]1[CH:24]=[CH:23][C:18]([C:19](=[N:21]O)[NH2:20])=[CH:17][CH:16]=1.O>C1C=CC=CC=1>[Cl:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]2[N:21]=[C:7]([C:3]3[O:4][CH:5]=[CH:6][C:2]=3[CH3:1])[O:9][N:20]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 781273-Methyl-2-furoic acidHCID 2246504-chloro-N'-hydroxybenzenecarboximidamide

Product 1

HCID 22147854HCID 22147854, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-methyl-furan-2-carboxylic acid (252 mg, 2 mmol), thionyl chloride (0.5 mL) in benzene (5 mL) was stirred at 60° C. for 8 h and evaporated to dryness. The residue was dissolved in pyridine (10 mL), and to the solution was added 4-chloro-benzamidoxime (340 mg, 2 mmol). The solution was refluxed for 10 h and then cooled to room temperature. The solution was diluted by water (20 mL) to produce a precipitate. The solid was collected by filtration and washed with water, then dried to yield 201 mg (39%) of the title compound. 1H NMR (CDCl3): 8.12 (d, J=8.4 Hz, 2H), 7.62 (d, J=1.5 Hz, 1H), 7.48 (d, J=8.4 Hz, 2H), 6.50 (d, J=1.5 Hz, 1H).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in pyridine (10 mL)
  3. temperatureThe solution was refluxed for 10 h
  4. customto produce a precipitate
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-33707b02f3e44d24ac767e4773a5e0d8
Source dataset
uspto-grants-2008_10
Patent number
US07435750B2

Reaction notes

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