Ethyl chloroformate → HCID 178473355, compound

HRID 443867Notes

Reaction equation

HRID 443867 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]1[NH:14][CH2:13][CH2:12][NH:11]1.[H-].[Na+].Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]1[NH:11][CH2:12][CH2:13][N:14]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 178478207HCID 178478207, compound

Product 1

HCID 178473355HCID 178473355, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 2-(2,4-dichlorophenylimino)imidazolidine (9.2 g.), sodium hydride (1.3 g. as 80% dispersion in oil) and tetrahydrofuran (65 ml.) was stirred and heated under reflux for 1 hour. The mixture was cooled and a solution of ethyl chloroformate (4.8 g.) in tetrahydrofuran (20 ml.) was added dropwise. The mixture was then stirred and heated under reflux for a further three hours. The mixture was cooled and then poured onto an ice-water mixture to give a solid which was dried over phosphorus pentoxide. Recrystallisation with charcoal from isopropanol gave 2-(2,4-dichlorophenylimino)-1-ethoxycarbonylimidazolidine, m.p. 138°-139° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe mixture was cooled
  4. stirringThe mixture was then stirred
  5. temperatureheated
  6. temperatureunder reflux for a further three hours
  7. temperatureThe mixture was cooled
  8. customto give a solid which
  9. dry with materialwas dried over phosphorus pentoxide
  10. customRecrystallisation with charcoal from isopropanol

Sources & evidence

ORD record
ord-d902082ac7d74738b59cd1bb419900c0
Source dataset
uspto-grants-1981_04
Patent number
US04262005

Reaction notes

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