Sodium Azide → HCID 178418535, compound
Reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9]CC)=[O:8])=[C:2]=[S:3].[N-:15]=[N+:16]=[N-:17].[Na+]>O>[C:7]([C:6]1[CH:5]=[C:4]([N:1]2[C:2]([SH:3])=[N:17][N:16]=[N:15]2)[CH:14]=[CH:13][CH:12]=1)([OH:9])=[O:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a mixture of 69 g of ethyl m-isothiocyanatobenzoate and 26 g of sodium azide was added 500 ml of water and the mixture was refluxed for 2 hours. After removing deposited insoluble matter by filtration, the filtrate was acidified by the addition of concentrated hydrochloric acid (pH about 2), and crystals of 1-(3-ethoxycarbonylphenyl)-5-mercaptotetrazole thus deposited were collected by filtration, mixed with 30 g of sodium hydroxide and 300 ml of water, and the mixture was stirred for 30 minutes at 70° C. The reaction mixture was neutralized by concentrated hydrochloric acid and crystals thus deposited were collected by filtration. The crude crystals were recrystallized from methanol to provide 32 g of 1-(3-carboxyphenyl)-5-mercaptotetrazole. The yield was 42% and the mleting point of the product was 181°-182° C.
Workup
- temperaturethe mixture was refluxed for 2 hours
- customAfter removing
- filtrationby filtration
- additionthe filtrate was acidified by the addition of concentrated hydrochloric acid (pH about 2), and crystals of 1-(3-ethoxycarbonylphenyl)-5-mercaptotetrazole
- filtrationthus deposited were collected by filtration
- additionmixed with 30 g of sodium hydroxide and 300 ml of water
- filtrationthus deposited were collected by filtration
- customThe crude crystals were recrystallized from methanol
Sources & evidence
- ORD record
- ord-58f86b367ad040acad259e2982cebc04
- Source dataset
- uspto-grants-1988_04
- Patent number
- US04737452
Reaction notes
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