Carbon Disulfide → HCID 13091644, compound

HRID 1758323Notes

Reaction equation

HRID 1758323 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]1[CH:9]=[CH:8][CH:7]=[CH:6]1.[CH3:10][N:11]1[C:15](CCCC(Cl)=S)=[N:14][N:13]=[N:12]1.[C:22](=[S:24])=S>>[CH3:10][N:11]1[C:15]([S:24][CH2:22][CH2:8][CH2:7][C:6]([C:6]2[O:5][CH:9]=[CH:8][CH:7]=2)=[O:5])=[N:14][N:13]=[N:12]1

Participants

5

Reactant 4

HCID 6348Carbon DisulfideHCID 8029FuranHCID 6451240Aluminum(III) ChlorideHCID 20509837HCID 20509837, compound

Product 1

HCID 13091644HCID 13091644, compound

Procedure

Aluminum chloride (4 g) is suspended in carbon disulfide (20 ml) and furan (1.5 g) is added to the suspension. 4-(1-Methyl-1,2,3,4-tetrazol-5-yl)thiobutyryl chloride (4.4 g) added dropwise to the mixture with stirring under ice-cooling, and the mixture is stirred at the same temperature for 1 hour. The reaction mixture is poured into hydrochloric acid-ice and extracted with chloroform. The chloroform solution is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride and dried over magnesium sulfate. After chloroform is distilled off, the residue is purified by column chromatography (Wakogel C-200, eluting agent, chloroform), the eluate is recrystallized from hexane-ether to give 1-methyl-5-[3-(2-furoyl)propyl]thio-1,2,3,4-tetrazole (0.8 g) as colorless needles, m.p. 41°-42° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at the same temperature for 1 hour
  3. extractionextracted with chloroform
  4. washThe chloroform solution is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationAfter chloroform is distilled off
  7. customthe residue is purified by column chromatography (Wakogel C-200, eluting agent, chloroform)
  8. customthe eluate is recrystallized from hexane-ether

Sources & evidence

ORD record
ord-745e93cba42544d6a6876eaf07bcbad8
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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