Hydrochloric Acid → 1,2-Thiazole-5-carbohydrazide

HRID 1889026Notes

Reaction equation

HRID 1889026 reaction equation
[S:1]1[C:5]([C:6]([NH:8][NH:9]C(OC(C)(C)C)=O)=[O:7])=[CH:4][CH:3]=[N:2]1.Cl>CO>[S:1]1[C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66599179HCID 66599179, compound

Product 1

HCID 552818681,2-Thiazole-5-carbohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1,1-dimethylethyl 2-(5-isothiazolylcarbonyl)hydrazinecarboxylate (I83) (480 mg, 1.973 mmol) in HCl (2 ml, 8.00 mmol) (4M in 1,4-dioxan) was stirred at room temperature under argon for 18 hours (overnight). After this time, the mixture was concentrated under reduced pressure to give a pale yellow coloured solid. The solid was dissolved in MeOH and passed through and SCX cartridge, eluting initially with MeOH and then with 2M NH3 in MeOH. The NH3/MeOH fractions were concentrated under reduced pressure to give a yellow coloured solid in 217 mg.

Workup

  1. concentrationAfter this time, the mixture was concentrated under reduced pressure
  2. customto give a pale yellow coloured solid
  3. washeluting initially with MeOH
  4. concentrationThe NH3/MeOH fractions were concentrated under reduced pressure
  5. customto give a yellow coloured solid in 217 mg

Sources & evidence

ORD record
ord-f2529446cf7d489fa598a871347a2e86
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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