Phosphorus oxychloride → HCID 19605030, compound

HRID 1603484Notes

Reaction equation

HRID 1603484 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([O:9][CH2:10][C:11]1[S:15][C:14]([CH2:16][NH:17][CH:18]=O)=[N:13][CH:12]=1)(=[O:8])[CH3:7]>C1(C)C=CC=CC=1>[C:6]([O:9][CH2:10][C:11]1[S:15][C:14]2=[CH:16][N:17]=[CH:18][N:13]2[CH:12]=1)(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19605015HCID 19605015, compound

Product 1

HCID 19605030HCID 19605030, compoundYield 61,116.199%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A 3.8 ml potion of phosphorus oxychloride was added to 8.7 ml of a toluene solution containing 1.74 g of 5-acetoxymethyl-2-(N-formylamino)methylthiazole, followed by stirring at 100° C. for 2 hours. Then, the solvent was evaporated under reduced pressure, and to the residue, 70 ml of chloroform and 52 ml of an aqueous saturated sodium bicarbonate solution were then added. After stirring, the organic layer was separated. The aqueous layer was extracted with chloroform (26 ml×2). The combined organic layer was combined, and then washed once with the aqueous saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by a silica gel column chromatograph to obtain 974 g of the title compound.

Workup

  1. customThen, the solvent was evaporated under reduced pressure
  2. additionto the residue, 70 ml of chloroform and 52 ml of an aqueous saturated sodium bicarbonate solution were then added
  3. stirringAfter stirring
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with chloroform (26 ml×2)
  6. washwashed once with the aqueous saturated sodium bicarbonate solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure
  10. customThe resulting residue was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-9e10cd01465a4735aa46823136d6be69
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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