Hydrochloric Acid → HCID 178423709, compound

HRID 363746Notes

Reaction equation

HRID 363746 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)#[N:2].C([N:18](CC)CC)C.S.[NH2:24][NH2:25].N([O-])=O.[Na+].Cl>C(O)C>[NH:24]1[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[N:2][N:18]=[N:25]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 9321HydrazineHCID 1455122-Cyano-4'-methylbiphenylHCID 23668193Sodium Nitrite

Product 1

HCID 178423709HCID 178423709, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, 26.9 mmol of 2-cyano-4'-methyl-1,1'-biphenyl was dissolved in 150 ml of ethanol, and 53.9 mmol of triethylamine and 105 mmol of hydrogen sulfide were added to the solution at room temperature, followed by adding 134.5 mmol of anhydrous hydrazine and keeping at the reflux temperature for 48 hours. The reaction mixture was warmed. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in 100 ml of ethanol added thereto, and 108 mmol of sodium nitrite and 100 ml of concentrated hydrochloric acid was added at 0° C. After keeping at 0°-5° C. for 2 hours, the reaction mixture was extracted with ethyl acetate to give 2-(tetrazol-5-yl)-4'-methyl-1,1'-biphenyl. Yield, 52%

Workup

  1. temperatureThe reaction mixture was warmed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 100 ml of ethanol
  4. additionadded
  5. waitAfter keeping at 0°-5° C. for 2 hours
  6. extractionthe reaction mixture was extracted with ethyl acetate

Sources & evidence

ORD record
ord-b65ec69013b448d88aa738415440cbdc
Source dataset
uspto-grants-1999_02
Patent number
US05874593

Reaction notes

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