Salicylic Acid → HCID 178522659, compound

HRID 1632215Notes

Reaction equation

HRID 1632215 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].O.[NH2:12][C:13]1[NH:17][N:16]=[N:15][N:14]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>O>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([NH:12][C:13]1[NH:17][N:16]=[N:15][N:14]=1)=[O:10]

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 178509300HCID 178509300, compound

Product 1

HCID 178522659HCID 178522659, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1.4 g (0.01 mole) of salicylic acid and 1.03 g (0.01 mole) of 5-aminotetrazole monohydrate in 40 ml. of pyridine was added dropwise 1.0 g (0.008 mole) of thionyl chloride. The mixture was stirred for one hour at 50° C. The stirred mixture was poured into water, acidified, and cooled. The resulting precipitate was collected by filtration and recrystallized from ethanol to provide 1.2 g 2-hydroxy-N-(tetrazol-5-yl)benzamide, in the form of a white solid, m.p. 264°-266° C.

Workup

  1. temperaturecooled
  2. filtrationThe resulting precipitate was collected by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ee5244a0c7814a4d9da7ebba88404c1f
Source dataset
uspto-grants-1984_10
Patent number
US04474792

Reaction notes

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