Hydrogen Sulfide → HCID 178525871, compound

HRID 1764773Notes

Reaction equation

HRID 1764773 reaction equation
[C:1]([CH2:6][NH:7][CH2:8][CH2:9][N:10]1[C:14]([S:15]CC2C=CC(OC)=CC=2)=[N:13][N:12]=[N:11]1)([O:3]CC)=[O:2].CO.S>O>[C:1]([CH2:6][NH:7][CH2:8][CH2:9][N:10]1[C:14](=[S:15])[NH:13][N:12]=[N:11]1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 887MethanolHCID 20331943HCID 20331943, compound

Product 1

HCID 178525871HCID 178525871, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 12.5 g. (35.6 mmol) 1-[2-[[(carbethoxy)methyl]amino]ethyl]-5-[(4-methoxybenzyl)thio]-1H-tetrazole in 250 ml. of methanol and 65 ml. of water was added a solution of 25.5 g. (80 mmol) of mercuric acetate in 80 ml. of water. The mixture was stirred at room temperature for 15 hours and at reflux for 1 hour. After thorough cooling, the mixture was treated with hydrogen sulfide gas for 1.5 hours. The dark mixture was heated over a steam bath for 1.5 hours and filtered. The filtrate was evaporated in vacuo to dryness. The residue was recrystallized from ethyl acetate to give 5.9 g. of 1-[2-[(carboxymethyl)amino]ethyl]-1,4-dihydro-5H-tetrazole-5-thione (82.8% yield) mp 215°-220° dec.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureThe dark mixture was heated over a steam bath for 1.5 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo to dryness
  5. customThe residue was recrystallized from ethyl acetate
  6. customto give 5.9 g

Sources & evidence

ORD record
ord-3884f8b715b141b3b1b87162c4031730
Source dataset
uspto-grants-1978_09
Patent number
US04117125

Reaction notes

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