Hydrochloric Acid → L-158507

HRID 2372839Notes

Reaction equation

HRID 2372839 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 r.t. The mixture was refluxed for 24 h, cooled to r.t., 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 r.t. to give a clear solution (45 min). Addition of HCl gas was continued for another 20 min. with stirring whereupon a white precipitate formed. The reaction mixture was stirred over night. 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 h
  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 r.t.
  7. customto give a clear solution (45 min)
  8. customformed
  9. stirringThe reaction mixture was stirred over night
  10. filtrationThe solid product was filtered
  11. washwashed with toluene
  12. customdried under vacuum

Sources & evidence

ORD record
ord-fa24ee9abc1f4f10b031d1fc408a9b00
Source dataset
uspto-grants-1992_03
Patent number
US05100897

Reaction notes

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