Water → HCID 21182303, compound

HRID 1386620Notes

Reaction equation

HRID 1386620 reaction equation
[OH:1][NH:2][C:3](=[NH:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]CC)=[CH:6][CH:5]=1.[Cl-].[CH3:21][O:22][C:23](=[O:33])[C:24]1[CH:32]=[CH:31][C:27]([C:28](O)=O)=[CH:26][CH:25]=1.O>N1C=CC=CC=1.O1CCCC1>[CH2:11]([O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]2[N:19]=[C:28]([C:27]3[CH:31]=[CH:32][C:24]([C:23]([O:22][CH3:21])=[O:33])=[CH:25][CH:26]=3)[O:1][N:2]=2)=[CH:9][CH:8]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 962WaterHCID 53442854Terephthalic acid monomethylester chlorideHCID 178443722HCID 178443722, compound

Product 1

HCID 21182303HCID 21182303, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-Hydroxy-4-octyloxybenzamidine (1.89 g) in pyridine (10 ml) was added terephthalic acid monomethyl ester chloride (1.67 g) in tetrahydrofuran (15 ml) dropwise at 0° C. The mixture was stirred at room temperature for 15 minutes, and poured into water. The precipitate was collected by filtration, dried and dissolved in pyridine (10 ml). The solution was refluxed for 1 hour. The reaction mixture was diluted with ethyl acetate and washed with 1N HCl, water and brine. The separated organic layer was dried over magnesium sulfate and the solvents were removed under reduced pressure. The residue was triturated with acetonitrile and collected by filtration. The solid was dried to give Methyl 4-[3-(4-n-hexyloxyphenyl)-1,2,4-oxadiazol-5-yl]benzoate (2.27 g).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried
  3. dissolutiondissolved in pyridine (10 ml)
  4. temperatureThe solution was refluxed for 1 hour
  5. additionThe reaction mixture was diluted with ethyl acetate
  6. washwashed with 1N HCl, water and brine
  7. dry with materialThe separated organic layer was dried over magnesium sulfate
  8. customthe solvents were removed under reduced pressure
  9. customThe residue was triturated with acetonitrile
  10. filtrationcollected by filtration
  11. customThe solid was dried

Sources & evidence

ORD record
ord-cb3eb4db8e57494ea674987f39070768
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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