Ethanol → Ethyl N-phenylglycinate hydrochloride

HRID 1445955Notes

Reaction equation

HRID 1445955 reaction equation
O=S(Cl)[Cl:3].[C:5]1([NH:11][CH2:12][C:13]([OH:15])=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:16](O)[CH3:17]>>[ClH:3].[CH2:16]([O:14][C:13](=[O:15])[CH2:12][NH:11][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 66025N-Phenylglycine

Product 1

HCID 12241367Ethyl N-phenylglycinate hydrochlorideYield 98%

Procedure

22 mL of SOCl2 were added dropwise to a solution of 30 g of phenylglycin 1 (198.5 mmol) in 200 mL of anhydrous ethanol. A gentle reflux occurred spontaneously and it was maintained for 3 h. The reaction was allowed to cool to room temperature and was stirred overnight. The solvent was removed under vacuum to afford 41.8 g of 2 as a white powder (98% yield).

Workup

  1. temperatureA gentle reflux
  2. temperatureit was maintained for 3 h
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-0d7aa126c51e4c17a65bde4d90e4e715
Source dataset
uspto-grants-2010_02
Patent number
US07666907B2

Reaction notes

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