Diethyl Ether → HCID 136088519, compound

HRID 227656Notes

Reaction equation

HRID 227656 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([OH:7])[N:6]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14].C(OCC)C>C(O)(=O)C>[C:13]([NH:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([OH:7])[N:6]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 2244655-Thiazolecarboxylicacid,2-amino-4-hydroxy-,ethylester(9CI)

Product 1

HCID 136088519HCID 136088519, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 2-amino-4-hydroxy-1,3-thiazole-5-carboxylate (6.00 g, 31.9 mmol) was dissolved in 100 mL of acetic acid with stirring. Acetic anhydride (15.0 mL, 159 mmol) was added via syringe. The reaction was stirred for 16 hours and 100 mL of diethyl ether was added. The reaction was filtered and the pale yellow solid was washed with diethyl ether, dried, and collected to afford 6.04 g (82%) of ethyl 2-(acetylamino)-4-hydroxy-1,3-thiazole-5-carboxylate. 1H NMR (300 MHz, DMSO-d6) δ 12.32 (s, 1H), 11.32 (s, 1H), 4.16 (q, J=7.0 Hz, 2H), 2.16 (s, 3H), 1.23 (t, J=7.0 Hz, 3H).

Workup

  1. stirringThe reaction was stirred for 16 hours
  2. filtrationThe reaction was filtered
  3. washthe pale yellow solid was washed with diethyl ether
  4. customdried
  5. customcollected

Sources & evidence

ORD record
ord-5bb04ea29b194249901b37581aa15972
Source dataset
uspto-grants-2009_07
Patent number
US07560568B2

Reaction notes

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