Triethylamine → HCID 20163524, compound

HRID 256301Notes

Reaction equation

HRID 256301 reaction equation
Cl[CH2:2][C:3]1[CH:10]=[C:7]([CH:8]=[O:9])[C:6]([OH:11])=[CH:5][CH:4]=1.[C:12]1([N:18]2[C:22]([SH:23])=[N:21][N:20]=[N:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>O1CCOCC1>[C:12]1([N:18]2[C:22]([S:23][CH2:2][C:3]3[CH:4]=[CH:5][C:6]([OH:11])=[C:7]([CH:8]=[O:9])[CH:10]=3)=[N:21][N:20]=[N:19]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3352915-(Chloromethyl)-2-hydroxybenzaldehydeHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 20163524HCID 20163524, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

25.6 g of 5-chloromethylsalicylaldehyde and 26.7 g of 1-phenyl-5-mercaptotetrazole were dissolved in 250 ml of dioxane. Then, internal temperature of the solution was lowered to 20° C. or less with ice water and thereto was added dropwise 20.8 ml of triethylamine with stirring followed by stirring at room temperature for 2 hours. After completion of the reaction, the precipitated salt was filtered off and the filtrate was concentrated under reduced pressure. Thus obtained residue was dissolved in 500 ml of ethyl acetate and then washed with water and the organic layer was dried over anhydrous sodium sulfate. Thereafter sodium sulfate was filtered off and the solvent was distilled out under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and cyclohexane.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. customAfter completion of the reaction
  3. filtrationthe precipitated salt was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThus obtained residue was dissolved in 500 ml of ethyl acetate
  6. washwashed with water
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. filtrationThereafter sodium sulfate was filtered off
  9. distillationthe solvent was distilled out under reduced pressure
  10. customThe residue was recrystallized from a mixed solvent of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-37408be93d6d469792cf618cd9090cbf
Source dataset
uspto-grants-1987_10
Patent number
US04702999

Reaction notes

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