4-Aminothiophenol → 4-(1H-Tetrazol-1-yl)benzene-1-thiol

HRID 259145Notes

Reaction equation

HRID 259145 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[N-:9]=[N+:10]=[N-:11].[Na+].[CH:13](OCC)(OCC)OCC>C(O)(=O)C>[N:1]1([C:2]2[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=2)[CH:13]=[N:11][N:10]=[N:9]1

Participants

5

Reactant 3

HCID 145104-AminothiophenolHCID 31214Ethyl orthoformateHCID 33557Sodium Azide

Product 1

HCID 214232364-(1H-Tetrazol-1-yl)benzene-1-thiol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

Alternatively a mixture of p-aminothiophenol (9.0 g.), sodium azide (7.0 g.), triethyl orthoformate (30 ml.), and acetic acid (30 ml.) was stirred and heated at 85° C. for 30 minutes. The reaction mixture was evaporated at reduced pressure and diluted with water to give a crystalline product which was collected and recrystallized from chloroform:hexane.

Workup

  1. customThe reaction mixture was evaporated at reduced pressure
  2. additiondiluted with water
  3. customto give a crystalline product which
  4. customwas collected
  5. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-d3f36e28225b49ea9b790d0861c0b1e0
Source dataset
uspto-grants-1977_07
Patent number
US04036849

Reaction notes

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