Phosphorus oxychloride → N-(4-Chloro-1,3-thiazol-2-yl)acetamide

HRID 1430168Notes

Reaction equation

HRID 1430168 reaction equation
O=[C:2]1[CH2:6][S:5][C:4]([NH:7][C:8](=[O:10])[CH3:9])=[N:3]1.O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:2]1[N:3]=[C:4]([NH:7][C:8](=[O:10])[CH3:9])[S:5][CH:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 539709N-(4-oxo-4,5-dihydrothiazol-2-yl)acetamide

Product 1

HCID 57417100N-(4-Chloro-1,3-thiazol-2-yl)acetamide

Conditions

Temperature
105 °C

Procedure

A mixture of N-(4-oxo-4,5-dihydro-thiazol-2-yl)-acetamide (Step 129.2) (14.8 g, 94 mmol) and POCl3 (175 mL, 20 eq) is heated to 105° C., stirred for 15 min, allowed to cool and concentrated. The residue is poured onto ice-H2O and extracted with EtOAc (2×100 mL). The organic phase is washed with a saturated solution of NaHCO3 (2×100 mL), dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH, 99:1) to afford 13.9 g of the title compound as a white solid: ESI-MS: 177.0 [M+H]+; tR=2.74 min (System 1); TLC: Rf=0.66 (DCM/MeOH, 9:1).

Workup

  1. temperatureto cool
  2. concentrationconcentrated
  3. additionThe residue is poured onto ice-H2O
  4. extractionextracted with EtOAc (2×100 mL)
  5. washThe organic phase is washed with a saturated solution of NaHCO3 (2×100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by silica gel column chromatography (DCM/MeOH, 99:1)

Sources & evidence

ORD record
ord-a8496d0a31ee4ceb9087dda79dc65732
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

Loading…