Ethyl chloroformate → HCID 12926196, compound

HRID 2195528Notes

Reaction equation

HRID 2195528 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(Cl)Cl.CO>C1COCC1.CN(C)C1C=CN=CC=1.O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 10928Ethyl chloroformateHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 81531DiisopropylethylamineHCID 21226129Dichloromethane methanol

Product 1

HCID 12926196HCID 12926196, compoundYield 80.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-fluorophenylhydrazine hydrochloride (2 g, 12.05 mmol) in THF (60 mL) is added DIPEA (6 mL, 34.40 mmol), ethyl chloroformate (1.2 mL, 12.55 mmol) and 4-dimethylaminopyridine (0.16 g, 1.31 mmol). The mixture is stirred at RT for 4 hours. The reaction is diluted with water and extracted with EtOAc, the organic phase is washed with saturated aqueous sodium chloride, dried over Na2SO4 and concentrated. The residue is purified by column chromatography on silica gel, eluting with DCM then DCM:MeOH (80:1) to afford the title compound (1.92 g, 80.5% yield). MS (m/z): 199 (M+H).

Workup

  1. extractionextracted with EtOAc
  2. washthe organic phase is washed with saturated aqueous sodium chloride
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography on silica gel
  6. washeluting with DCM

Sources & evidence

ORD record
ord-3fb8bf2945994e29945f9bcd8b4b114c
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Reaction notes

Loading…