Ethyl chloroformate → HCID 23323503, compound

HRID 1381128Notes

Reaction equation

HRID 1381128 reaction equation
[H-].[Na+].[F:3][C:4]([F:24])([F:23])[C:5]1[CH:6]=[C:7]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[NH:19][CH2:20][CH2:21][N:22]=2)[CH:8]=[CH:9][CH:10]=1.[H][H].Cl[C:28](OCC)=[O:29]>O1CCCC1.O.C(O)(=O)C>[F:24][C:4]([F:3])([F:23])[C:5]1[CH:6]=[C:7]([N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:18]3=[N:19][CH2:20][CH2:21][N:22]3[C:28]2=[O:29])[CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 23323490HCID 23323490, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23323503HCID 23323503, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.26 g (75 mmol) of sodium hydride were added to a solution of 10.4 g (34 mmol) of 2-(2-(3-trifluoromethylphenylamino)-phenyl)-2-imidazoline in 100 ml of absolute tetrahydrofuran, and the mixture was warmed to 50° to 60° C. until evolution of hydrogen had ceased (5 to 6 hours). After the reaction mixture had cooled to room temperature, 16 ml (0.166 mol) of ethyl chloroformate were added dropwise to it and it was boiled under reflux for one hour. The mixture was allowed to cool, the pH was adjusted to 4-5 with glacial acetic acid, and the mixture was diluted with water and extracted with dichloromethane. The organic phase was dried over Na2SO4 and concentrated, and the residue was subjected to chromatography over silica gel (running agent ethyl acetate/methanol 7:3), and the residue from the evaporation of the product-containing fractions was thoroughly stirred with ether/petroleum ether 1:3.

Workup

  1. custom(5 to 6 hours)
  2. temperatureunder reflux for one hour
  3. temperatureto cool
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. customthe residue from the evaporation of the product-containing fractions

Sources & evidence

ORD record
ord-73da63180da24844802865ff98f0b639
Source dataset
uspto-grants-1986_04
Patent number
US04585772

Reaction notes

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