Thionyl Chloride → 1-(2-Chloroethyl)imidazolidin-2-one

HRID 1241415Notes

Reaction equation

HRID 1241415 reaction equation
O[CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9].S(Cl)([Cl:12])=O>C(Cl)(Cl)Cl>[Cl:12][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 77290Hydroxyethyl imidazolidinone

Product 1

HCID 754351-(2-Chloroethyl)imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5.00 g (38.42 mmol) of 1-(2-hydroxyethyl)imidazolidin-2-one 44-1 and 3.82 mL (52.39 mmol) of thionyl chloride in 75 mL of chloroform was stirred at reflux for 4 hours. The reaction was concentrated in vacuo to an orange oil, which was redissolved in chloroform and washed twice with water. The organic layer was dried and reconcentrated to give the crude desired product as an orange solid. The solid was used as obtained from the reaction without further purification.

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationThe reaction was concentrated in vacuo to an orange oil, which
  3. dissolutionwas redissolved in chloroform
  4. washwashed twice with water
  5. customThe organic layer was dried

Sources & evidence

ORD record
ord-ff3f860f751f48c6810f91e872bc611d
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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