Phosphorus oxychloride → Ethyl 2-chloro-4-methyl-1,3-thiazole-5-carboxylate

HRID 1173038Notes

Reaction equation

HRID 1173038 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=O)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:4]1[S:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([CH3:1])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11074139Ethyl 2-hydroxy-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 594903Ethyl 2-chloro-4-methyl-1,3-thiazole-5-carboxylateYield 86%

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 4-methyl-2-oxo-2,3-dihydro-1,3-thiazole-5-carboxylate (0.57 g, 3.05 mmol) and POCl3 (5 mL) was heated at 120° C. for 18 h. Upon cooling, the mixture was concentrated. Water (15 mL) was slowly added and stirred for 10 min. The mixture was extracted with Et2O (3×15 mL). The combined organics were dried with MgSO4 and concentrated. The crude material was purified by chromatography (EtOAc/hexanes) to give the title compound as a white solid (0.54 g, 86%). 1H NMR (400 MHz, CDCl3) δ 4.32 (q, J=7.1 Hz, 2H), 2.68 (s, 3H), 1.35 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureUpon cooling
  2. concentrationthe mixture was concentrated
  3. additionWater (15 mL) was slowly added
  4. extractionThe mixture was extracted with Et2O (3×15 mL)
  5. dry with materialThe combined organics were dried with MgSO4
  6. concentrationconcentrated
  7. customThe crude material was purified by chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-5cb1019904b04fcd937f72f09785de3a
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

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