Hydrochloric Acid → HCID 178477931, compound

HRID 426311Notes

Reaction equation

HRID 426311 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[C:10]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH:9]=2)=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[NH:25][N:24]=[N:23][N:15]=3)[CH:11]=[C:10]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 66702491HCID 66702491, compound

Product 1

HCID 178477931HCID 178477931, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4,4″-Dichloro-[1,1′;3′,1″]terphenyl-5′-carbonitrile (50 mg, 0.15 mmol), sodium azide (20 mg, 0.31 mmol) and ammonium chloride (16 mg, 0.31 mmol) in DMF (1 mL) was heated at 100° C. for 16 h. The reaction mixture was acidified with 1M HCl solution poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and the solvent was removed in vacuo to give 5-(4,4″-dichloro-[1,1′;3′,1″]terphenyl-5′-yl)-1H-tetrazole yield 36 mg (64%) as an off-white solid. 1H NMR (DMSO) δ 7.49 (d, 2H), 7.23 (t, 1H), 7.17 (s br, 1H), 6.96-6.99 (m, 4H), 6.71-6.74 (m, 4H), LCMS method A R.T. 3.5

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-36920c6e24194149b4e69006f37a38cb
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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