Hydrogen Sulfide → HCID 178478026, compound

HRID 636256Notes

Reaction equation

HRID 636256 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C([N:12](CC)CC)C.S.[NH2:18][NH2:19].N([O-])=O.[Na+]>CO>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]1[NH:5][N:12]=[N:19][N:18]=1

Participants

7

Reactant 5

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 9321HydrazineHCID 133912-ChlorobenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 178478026HCID 178478026, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

First, 35.6 mmol of 2-chlorobenzonitrile was dissolved in 50 ml of methanol, and 35.6 mmol of triethylamine and 105 mmol of hydrogen sulfide were added thereto at room temperature, followed by adding 180 mmol of anhydrous hydrazine and keeping at the reflux temperature for 48 hours. The reaction mixture was evaporated under reduced pressure. The residue was dissolved in 50 ml of 5% hydrochloric acid, and 75 mmol of sodium nitrite was added thereto at 0° C. to cause reaction. After completion of the reaction, the reaction mixture was extracted with ethyl acetate to give 5-(2-chlorophenyl)tetrazole. Yield, 54%

Workup

  1. customat room temperature
  2. customThe reaction mixture was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in 50 ml of 5% hydrochloric acid
  4. customat 0° C.
  5. customreaction
  6. customAfter completion of the reaction
  7. extractionthe reaction mixture was extracted with ethyl acetate

Sources & evidence

ORD record
ord-43d44fb86f0d4bcdbdd9a8df4407281f
Source dataset
uspto-grants-2001_02
Patent number
US06191289B1

Reaction notes

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