Ethyl chloroformate → HCID 59191272, compound

HRID 1023939Notes

Reaction equation

HRID 1023939 reaction equation
[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=2[F:15])=[C:5]([O:18][CH3:19])[CH:4]=1)[CH3:2].[CH2:20]([O:22][C:23](Cl)=[O:24])[CH3:21].[NH4+].[Cl-]>C1COCC1.C([O-])(O)=O.[Na+]>[CH2:20]([O:22][C:23](=[O:24])[NH:12][C:11]1[CH:13]=[CH:14][C:8]([O:7][C:6]2[CH:16]=[CH:17][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=2[O:18][CH3:19])=[C:9]([F:15])[CH:10]=1)[CH3:21]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 59191245HCID 59191245, compound

Product 1

HCID 59191272HCID 59191272, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 86639098HCID 86639098, compoundSolvent

Procedure

4-(4-ethyl-2-methoxyphenoxy)-3-fluoroaniline (0.19 mmol; 50 mg) in 1 mL THF/NaHCO3 sat. (1/1), at 0° C. were added ethylchloroformate (0.38 mmol; 41 mg). The reaction was stirred overnight at room temperature. The mixture was hydrolysed with NH4Cl sat.(4 mL) and extracted with dichloromethane (3*2 mL). Combined organic phases were dried over Na2SO4, concentrated in vacuo. The title compound (36 mg; 56%) was obtained as a brown oil, after purification by preparative TLC on silica gel (ethyl acetate/cyclohexane—70/30).

Workup

  1. extractionextracted with dichloromethane (3*2 mL)
  2. dry with materialCombined organic phases were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1b3e4d387bf417c9c2619939fbf0cab
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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