Methanol → HCID 69068627, compound

HRID 660890Notes

Reaction equation

HRID 660890 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH2:10][C:11]([OH:13])=[O:12].S(Cl)([Cl:18])=O.[CH3:20]O>>[ClH:18].[CH3:20][O:12][C:11](=[O:13])[CH2:10][NH:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:14])([F:15])[F:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 21238931HCID 21238931, compound

Product 1

HCID 69068627HCID 69068627, compound

Procedure

300 mg (1.37 mmol) of DL-[2-(trifluoromethyl)phenyl]-glycine are placed in 9 ml methanol and slowly treated at RT with 130 μl thionyl chloride. The solution is heated overnight under reflux, then cooled to RT and freed of the volatile components on the rotary evaporator. Since by LC/MS the residue still contains ca. 44% educt, it is reacted again under the conditions described above. After this, the conversion is complete. 371 mg (93% of theory) of the title compound are obtained.

Workup

  1. temperatureThe solution is heated overnight
  2. temperatureunder reflux
  3. customfreed of the volatile components on the rotary evaporator
  4. customSince by LC/MS the residue still contains ca. 44% educt, it is reacted again under the conditions

Sources & evidence

ORD record
ord-3af4c6cbbde34aa0812e33b0124a5491
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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