Ethyl chloroformate → HCID 23323488, compound

HRID 1381131Notes

Reaction equation

HRID 1381131 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[NH:21][CH2:22][CH2:23][N:24]=1.[H][H].Cl[C:28](OCC)=[O:29]>O1CCCC1.O.C(O)(=O)C>[F:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2=[N:21][CH2:22][CH2:23][N:24]2[C:28]1=[O:29]

Participants

8

Reactant 4

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 23323496HCID 23323496, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23323488HCID 23323488, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.1 g (25 mmol) of sodium hydride were added to a solution of 3.47 g (11.6 mmol) of 2-(2-(2-fluoro-4-nitrophenylamino)-phenyl)-2-imidazoline in 60 ml of absolute tetrahydrofuran, and the mixture was warmed to 50° C. until the evolution of hydrogen had ended. After the reaction mixture had been cooled to room temperature, 5.8 ml (60 mmol) of ethyl chloroformate in 10 ml of absolute tetrahydrofuran were added dropwise to it and it was warmed to 50° C. for 90 minutes. The reaction mixture was allowed to cool to room temperature, acidified with glacial acetic acid, diluted with water and extracted with dichloromethane. The organic phase was concentrated by evaporation, water was added to the residue, and the solution was adjusted to a pH of 1-2 with hydrochloric acid and was extracted with dichloromethane. The precipitate which occurred on addition of KHCO3 solution to the aqueous phase was filtered off under suction, washed with water and dried.

Workup

  1. temperaturewas warmed to 50° C. for 90 minutes
  2. temperatureto cool to room temperature
  3. extractionextracted with dichloromethane
  4. concentrationThe organic phase was concentrated by evaporation, water
  5. additionwas added to the residue
  6. extractionwas extracted with dichloromethane
  7. additionThe precipitate which occurred on addition of KHCO3 solution to the aqueous phase
  8. filtrationwas filtered off under suction
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-7f1740db3b4848c9b5cd3c4bcb26e13c
Source dataset
uspto-grants-1986_04
Patent number
US04585772

Reaction notes

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