Ethyl chloroformate → HCID 4243141, compound

HRID 651375Notes

Reaction equation

HRID 651375 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.Cl[C:14]([O:16][CH2:17][CH3:18])=[O:15]>N1C=CC=CC=1>[CH2:17]([O:16][C:14](=[O:15])[NH:7][C:6]1[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11])[CH3:18]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 667934-Methoxy-2-nitroaniline

Product 1

HCID 4243141HCID 4243141, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled solution of 4-methoxy-2-nitroaniline (25 g; 0.15 mol) in pyridine (370 ml), ethyl chloroformate (17.8 ml; 0.18 mol) was added dropwise. The mixture was refluxed for 10 hours, then cooled and poured into ice-water. The precipitated solid was collected and purified by flash chromatography (silica gel, eluent: hexane/diethyl ether 85:15) to yield the title compound as a yellow solid. 7.3 g; m.p. 56-57° C.

Workup

  1. temperatureThe mixture was refluxed for 10 hours
  2. temperaturecooled
  3. customThe precipitated solid was collected
  4. custompurified by flash chromatography (silica gel, eluent: hexane/diethyl ether 85:15)

Sources & evidence

ORD record
ord-6f9892b60abf4229b4ecf41fe813fe20
Source dataset
uspto-grants-2001_08
Patent number
US06281218B1

Reaction notes

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