Ammonium Chloride → HCID 178420853, compound

HRID 437592Notes

Reaction equation

HRID 437592 reaction equation
[CH:1]1[CH:5]=[C:4]([S:6][CH2:7][C:8]#[N:9])[S:3][CH:2]=1.[N-:10]=[N+:11]=[N-:12].[Na+].[Cl-].[NH4+].[Cl-].[Li+]>CN(C)C=O>[S:3]1[CH:2]=[CH:1][CH:5]=[C:4]1[S:6][CH2:7][C:8]1[NH:12][N:11]=[N:10][N:9]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 21429205HCID 21429205, compound

Product 1

HCID 178420853HCID 178420853, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7.76 g. (50 millimoles) of thiophene-2-thioacetonitrile, 4.30 g. (66 millimoles) of sodium azide, 3.55 g. (66 millimoles) of ammonium chloride, and 0.38 g. (9 millimoles) of lithium chloride is maintained for 5 hours at 120° in 50 ml. of dry dimethylformamide. The dimethylformamide is withdrawn under vacuum, the residue is combined with 500 ml. of cold 0.2 N sodium hydroxide solution and extracted with ether. The aqueous phase is adjusted to pH 3 and extracted three times with respectively 150 ml. of ether. The ether phase yields, after drying (Na2SO4) and concentration, the crude, solid tetrazole which is recrystallized once from acetonitrile/water and once from ethanol/water.

Workup

  1. additionA mixture of 7.76 g
  2. customThe dimethylformamide is withdrawn under vacuum
  3. extractionof cold 0.2 N sodium hydroxide solution and extracted with ether
  4. extractionextracted three times with respectively 150 ml
  5. customThe ether phase yields
  6. customafter drying
  7. concentration(Na2SO4) and concentration
  8. customthe crude, solid tetrazole which is recrystallized once from acetonitrile/water and once from ethanol/water

Sources & evidence

ORD record
ord-bb604464a8444790a08ece4b8de05e57
Source dataset
uspto-grants-1977_06
Patent number
US04031236

Reaction notes

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