HCID 15098931, compound → HCID 178482028, compound

HRID 2290234Notes

Reaction equation

HRID 2290234 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12])=[N:5][N:4]=[N:3]1.N1C=CC=CC=1.[SH2:20]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][C:11]([OH:12])=[S:20])=[N:5][N:4]=[N:3]1

Participants

5

Reactant 2

HCID 15098931HCID 15098931, compoundHCID 18424405HCID 18424405, compound

Product 1

HCID 178482028HCID 178482028, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

920 mg of 4-(1-methyltetrazol-5-ylthio)-butyric acid chloride are dissoved in 1.4 ml of absolute methylene chloride and added dropwise at 0° to 5.54 ml of a pyridine/H2S solution in methylene chloride (30 ml of absolute pyridine and 6 g of H2S in 100 ml of methylene chloride). The whole is then stirred for one hour at 0° under a nitrogen atmosphere. The reaction mixture is taken up in chloroform, the aqueous phase is acidified to a pH of 2 using 2N H2SO4 and extraction is carried out twice with chloroform. The combined organic phases are washed twice with 5 ml of 10% NaHCO3 solution. The pH is then adjusted to 3 using 2N H2SO4 and the title compound is extracted several times with chloroform. The title compound is obtained after drying over sodium sulphate and concentrating.

Workup

  1. extraction2N H2SO4 and extraction
  2. washThe combined organic phases are washed twice with 5 ml of 10% NaHCO3 solution
  3. extractionthe title compound is extracted several times with chloroform

Sources & evidence

ORD record
ord-44bcabe2256946aaaa08fe368ad638d9
Source dataset
uspto-grants-1986_10
Patent number
US04616007

Reaction notes

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