Sodium Carbonate → 2-Amino-5-[[(5-ethyl-2-oxazolyl)methyl]thio]-thiazole

HRID 1637237Notes

Reaction equation

HRID 1637237 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([CH2:8][S:9][C:10]2[S:14][C:13]([NH:15]C(=O)C)=[N:12][CH:11]=2)=[N:5][CH:4]=1)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+]>Cl>[NH2:15][C:13]1[S:14][C:10]([S:9][CH2:8][C:6]2[O:7][C:3]([CH2:1][CH3:2])=[CH:4][N:5]=2)=[CH:11][N:12]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 5329663N-[5-[[(5-ethyl-2-oxazolyl)methyl]thio]-2-thiazolyl]acetamide

Product 1

HCID 186679822-Amino-5-[[(5-ethyl-2-oxazolyl)methyl]thio]-thiazoleYield 55%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-[5-[[(5-ethyl-2-oxazolyl)methyl]thio]-2-thiazolyl]acetamide (1.3 g, 4.6 mmol) in 1 N hydrochloric acid (15 mL) was stirred at 80-90° C. for 3 h. It was cooled to rt and the pH of the solution was adjusted to 7 with sodium carbonate. The product was extracted with methylene chloride (3×10 mL). The combined extract was dried over Na2SO4 and concentrated. The residue was triturated with ethyl ether and the precipitated solid was collected to afford 2-amino-5-[[(5-ethyl-2-oxazolyl)methyl]thio]-thiazole (610 mg, 55%) as a solid, mp 119-120° C. 1H NMR (CDCl3) δ6.93 (s, 1 H), 6.61 (s, 1 H), 5.41 (s, 2 H), 3.82 (s, 3 H), 2.62 (q, J=7.6 Hz, 2 H), 1.18 (t, J=7.6 Hz, 3 H); MS m/e 242 (M+H)+ ;

Workup

  1. extractionThe product was extracted with methylene chloride (3×10 mL)
  2. extractionThe combined extract
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was triturated with ethyl ether
  6. customthe precipitated solid was collected

Sources & evidence

ORD record
ord-49b23958409b4546bad02892ada6053e
Source dataset
uspto-grants-2000_03
Patent number
US06040321

Reaction notes

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