Hydrochloric Acid → Triazamate acid

HRID 129973Notes

Reaction equation

HRID 129973 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 86306Triazamate2×

Product 1

HCID 14299898Triazamate acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
200 °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 200° 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-3t-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-93cc996f09f94a5f82f31377dcb46132
Source dataset
uspto-grants-1995_11
Patent number
US05470984

Reaction notes

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