Hydrochloric Acid → L-158507

HRID 2255526Notes

Reaction equation

HRID 2255526 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[Sn]([N:20]=[N+:21]=[N-:22])(C)C.Cl>C1(C)C=CC=CC=1>[CH3:15][C:12]1[CH:11]=[CH:10][C:9]([C:4]2[C:3]([C:1]3[N:22]=[N:21][NH:20][N:2]=3)=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1455122-Cyano-4'-methylbiphenylHCID 5104973Azido(trimethyl)stannane

Product 1

HCID 9794697L-158507Yield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-cyano-4'-methylbiphenyl (390 g, 2.02 moles) in toluene (2.3 L) was added trimethyltin azide (525 g, 2.55 moles) at room temperature. The mixture was refluxed for 24 hours, cooled to room temperature, filtered, washed with toluene and sucked dry in a funnel. The precipitate was resuspended in toluene (3.5 L) and THF (250 mL) was added. Anhydrous HCl was bubbled in at a moderate rate at room temperature to give a clear solution (45 minutes). Addition of HCl gas was continued for another 20 minutes with stirring whereupon a white precipitate formed. The reaction mixture was stirred overnight. The solid product was filtered, washed with toluene followed with ether and then dried under vacuum. This produced 250 g (53% yield of the tetrazole. m.p. 152°-154° C.; 1H-NMR (CDCl3): 2.40 (s, 3H), 7.19 (dd, 1H), 7.55 (m, 2H), 8.25 (dd, 1H).

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. filtrationfiltered
  3. washwashed with toluene
  4. customsucked dry in a funnel
  5. additionTHF (250 mL) was added
  6. customAnhydrous HCl was bubbled in at a moderate rate at room temperature
  7. customto give a clear solution (45 minutes)
  8. customformed
  9. stirringThe reaction mixture was stirred overnight
  10. filtrationThe solid product was filtered
  11. washwashed with toluene
  12. customdried under vacuum

Sources & evidence

ORD record
ord-d0ba3c722d324844b4bd8da540267796
Source dataset
uspto-grants-1993_08
Patent number
US05240928

Reaction notes

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