Phosphorus oxychloride → HCID 57423981, compound

HRID 1875352Notes

Reaction equation

HRID 1875352 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:13]=[CH:12][S:11][CH:10]=1)=O.P(Cl)(Cl)(Cl)=O>C(Cl)(Cl)Cl>[CH3:1][O:2][CH2:3][C:4]1[C:10]2[S:11][CH:12]=[CH:13][C:9]=2[CH2:8][CH2:7][N:6]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 49694838HCID 49694838, compound

Product 1

HCID 57423981HCID 57423981, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

15.6 g (78.3 mmol) 2-methoxy-N-(2-thiophen-3-yl-ethyl)-acetamide are dissolved in 350 ml chloroform and combined with 35.8 ml (391.4 mmol) phosphorus oxychloride while cooling with an ice bath. The ice bath is removed and the mixture is refluxed for 5 hours. Then it is carefully added to 600 ml of warm sodium hydroxide solution (4N) and the aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried on sodium sulphate, filtered and evaporated down i. vac. The crude product is purified by flash chromatography on silica gel (eluant DCM/methanol 98:2→95:5).

Workup

  1. temperaturewhile cooling with an ice bath
  2. customThe ice bath is removed
  3. temperaturethe mixture is refluxed for 5 hours
  4. additionThen it is carefully added to 600 ml of warm sodium hydroxide solution (4N)
  5. extractionthe aqueous phase is extracted three times with ethyl acetate
  6. customThe combined organic phases are dried on sodium sulphate
  7. filtrationfiltered
  8. customevaporated down i
  9. customThe crude product is purified by flash chromatography on silica gel (eluant DCM/methanol 98:2→95:5)

Sources & evidence

ORD record
ord-b4e2a2dc2c2543e8bd689b3671a02cf9
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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