Potassium Carbonate → 1-Methyl-5-[3-(2-naphthoyl)propyl]thio-1,2,3,4-tetrazole

HRID 1758307Notes

Reaction equation

HRID 1758307 reaction equation
[CH3:1][N:2]1[C:6]([SH:7])=[N:5][N:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+].[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[C:24]([CH2:26][CH2:27][CH2:28]Cl)=[O:25]>CC(C)=O>[CH3:1][N:2]1[C:6]([S:7][CH2:28][CH2:27][CH2:26][C:24]([C:15]2[CH:16]=[CH:17][C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=2)=[O:25])=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122875592-(4-Chlorobutyryl)naphthaleneHCID 178482017HCID 178482017, compound

Product 1

HCID 130916401-Methyl-5-[3-(2-naphthoyl)propyl]thio-1,2,3,4-tetrazoleYield 51%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Methyl-5-mercapto-1,2,3,4-tetrazole (1.2 g), potassium carbonate (2.1 g) and 3-chloropropyl 2-naphthyl ketone (3.5 g) are added to acetone (50 ml) and the mixture is refluxed with stirring for 2 hours. The reaction mixture is concentrated to dryness under reduced pressure and the residue dissolved in chloroform. Insolubles are filtered off. The filtrated is concentrated and the residue is purified by silica gel column chromatography [Kieselgel 60, eluant: benzene-ether (10:1)] and the product is recrystallized from ethanol to obtain 1-methyl-5-[3-(2-naphthoyl)propyl]thio-1,2,3,4-tetrazole (yield 51%) as colorless prisms, m.p. 118°-120° C.

Workup

  1. temperaturethe mixture is refluxed
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  3. dissolutionthe residue dissolved in chloroform
  4. filtrationInsolubles are filtered off
  5. concentrationThe filtrated is concentrated
  6. customthe residue is purified by silica gel column chromatography [Kieselgel 60, eluant: benzene-ether (10:1)]
  7. customthe product is recrystallized from ethanol

Sources & evidence

ORD record
ord-3c70934276be439686996f6975bd570f
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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