Hydrochloric Acid → HCID 178524450, compound

HRID 648898

Reaction equation

HRID 648898 reaction equation
[N:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][CH:5]=1)=[C:2]=[S:3].[N-:15]=[N+:16]=[N-:17].[Na+].Cl>O>[C:8]([C:7]1[CH:13]=[CH:14][C:4]([N:1]2[C:2]([SH:3])=[N:17][N:16]=[N:15]2)=[CH:5][CH:6]=1)([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 71003Ethyl 4-isothiocyanatobenzoate

Product 1

HCID 178524450HCID 178524450, compoundYield 120.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Then, 31 g of ethyl p-isothiocyanatobenzoate and 11.7 g of sodium azide were dispersed in 300 ml of water and the dispersion was refluxed for 5 hours. The reaction mixture was cooled to room temperature and acidified (pH about 2) by the addition of concentrated hydrochloric acid. Crystals of 1-(4-ethoxycarbonylphenyl)-5-mercaptotetrazole thus deposited were collected by filtration and after adding thereto 25 g of sodium hydroxide and 500 ml of water, the mixture was stirred for 30 minutes at 70° C. The reaction mixture was cooled to room temperature, neutralized by the addition of concentrated hydrochloric acid, and crystals thus deposited were collected by filtration and recrystallized from methanol to provide 40 g of 1-(4-carboxyphenyl)-5-mercaptotetrazole. The yield was 48% and the melting point was 198° C.

Workup

  1. temperaturethe dispersion was refluxed for 5 hours
  2. filtrationCrystals of 1-(4-ethoxycarbonylphenyl)-5-mercaptotetrazole thus deposited were collected by filtration
  3. additionafter adding
  4. temperatureThe reaction mixture was cooled to room temperature
  5. additionneutralized by the addition of concentrated hydrochloric acid, and crystals
  6. filtrationthus deposited were collected by filtration
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-09ca77bdf0cc43acaceb3c71a6aa069e
Source dataset
uspto-grants-1988_04
Patent number
US04737452

Linked notes

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