Hydrochloric Acid → HCID 44632857, compound

HRID 2381786Notes

Reaction equation

HRID 2381786 reaction equation
[NH:1]([C:3]1[S:4][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([CH3:8])[N:7]=1)[NH2:2].Cl.[N:15]([O-])=O.[Na+]>C(OCC)C.O>[N:1]([C:3]1[S:4][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([CH3:8])[N:7]=1)=[N+:2]=[N-:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 748178ethyl 2-hydrazino-4-methyl-1,3-thiazole-5-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 44632857HCID 44632857, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a cooled (0° C.) suspension of ethyl 2-hydrazinyl-4-methylthiazole-5-carboxylate (3.00 g, 14.92 mmol) in a mixture of diethyl ether (15 mL) and water (15 mL) was added hydrochloric acid (2.72 mL) dropwise. The reaction mixture was stirred for 10 minutes, and a solution of sodium nitrite (1.21 g, 17.46 mmol) in water (2 mL) was added. The mixture was stirred for 2 hours at 0° C. and extracted with diethyl ether. The organic layer was separated, washed with brine, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate:hexanes, 1:4) to afford the title compound as a yellowish solid (1.49 g, 47%): 1H NMR (300 MHz, CDCl3) δ 4.29 (q, J=6.0 Hz, 2H), 2.62 (s, 3H), 1.33 (t, J=6.0 Hz, 3H); MS (ES+) m/z 213.2 (M+1).

Workup

  1. temperatureTo a cooled
  2. stirringThe mixture was stirred for 2 hours at 0° C.
  3. extractionextracted with diethyl ether
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (ethyl acetate:hexanes, 1:4)

Sources & evidence

ORD record
ord-c8048e0f1c6848ccb470f711f30dee05
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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