Hydrochloric Acid → HCID 178423709, compound

HRID 636257Notes

Reaction equation

HRID 636257 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 0C. 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-a5647feb26354297b20d388bb5196459
Source dataset
uspto-grants-2001_02
Patent number
US06191289B1

Reaction notes

Loading…