Hydrochloric Acid → HCID 13487717, compound

HRID 2368277Notes

Reaction equation

HRID 2368277 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[N:6]=[N:7][S:8][C:9]=1[NH:10]C(OC(C)(C)C)=O)=[O:4].Cl>O1CCOCC1>[CH3:1][NH:2][C:3]([C:5]1[N:6]=[N:7][S:8][C:9]=1[NH2:10])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70115888Carbamic acid, N-[4-[(methylamino)carbonyl]-1,2,3-thiadiazol-5-yl]-, 1,1-dimethylethyl ester

Product 1

HCID 13487717HCID 13487717, compoundYield 491.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-tert-butoxycarbonylamino-[1,2,3]thiadiazole-4-carboxylic acid methylamide (0.23 g, 0.9 mmol) in dioxane (4 ml) was treated with HCl (6 ml, 4M dioxane solution) at ambient temperature and stirred for 3 days. The solvent was evaporated, and the residue was suspended in diethylether, mixed and sucked off. The remaining solid material was dissolved in dichloromethane and extracted with NaOH (10 ml, 1M aqueous solution). The aqueous phase was extracted with dichloromethane, and the combined organic layers were dried and the solvent was evaporated to yield the product as colorless solid (0.7 g, 48%) which was used without any further purification.

Workup

  1. customThe solvent was evaporated
  2. additionmixed
  3. dissolutionThe remaining solid material was dissolved in dichloromethane
  4. extractionextracted with NaOH (10 ml, 1M aqueous solution)
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. customthe combined organic layers were dried
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-44f509b138574a6f834294f4a9e05626
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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