Hydrochloric Acid → Triazamate acid

HRID 1252157Notes

Reaction equation

HRID 1252157 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]([N:5]1[C:9]([S:10][CH2:11][C:12]([O:14]CC)=[O:13])=[N:8][C:7]([C:17]([CH3:20])([CH3:19])[CH3:18])=[N:6]1)=[O:4].Cl>C1COCC1>[CH3:1][N:2]([CH3:21])[C:3]([N:5]1[C:9]([S:10][CH2:11][C:12]([OH:14])=[O:13])=[N:8][C:7]([C:17]([CH3:19])([CH3:18])[CH3:20])=[N:6]1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86306Triazamate

Product 1

HCID 14299898Triazamate acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To 1.2 g of 1-dimethylcarbamoyl-3-t-butyl-5-carboethoxymethylthio-1H-1,2,4-triazole (the compound of Example 2) in 20 ml of THF was added 4 ml of 12M HCl. After stirring for 48 h at 20° C. the reaction mixture was partitioned between ether and water, the ether layer was extracted with dilute NaOH and the resulting aqueous layer was acidified and extracted with fresh ether. The resulting ether layer was dried over magnesium sulfate, filtered and evaporated under vacuum to yield 1-dimethylcarbamoyl-3-t-butyl-5-carboxymethylthio-1H-1,2,4-triazole as an oil.

Workup

  1. customwas partitioned between ether and water
  2. extractionthe ether layer was extracted with dilute NaOH
  3. extractionextracted with fresh ether
  4. dry with materialThe resulting ether layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-1d7b0b845d974955b99d01aaaf83b577
Source dataset
uspto-grants-1988_05
Patent number
US04742072

Reaction notes

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