Ethyl chloroformate → HCID 19832672, compound

HRID 2051097Notes

Reaction equation

HRID 2051097 reaction equation
[CH3:1][O:2][N:3]([CH3:15])[C:4](=[O:14])[C:5]1[CH:10]=[C:9]([NH2:11])[C:8]([F:12])=[CH:7][C:6]=1[Cl:13].Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>N1C=CC=CC=1>[Cl:13][C:6]1[C:5]([C:4](=[O:14])[N:3]([O:2][CH3:1])[CH3:15])=[CH:10][C:9]([NH:11][C:17](=[O:18])[O:19][CH2:20][CH3:21])=[C:8]([F:12])[CH:7]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 19832698HCID 19832698, compound

Product 1

HCID 19832672HCID 19832672, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

55.6 g of N-methoxy-N-methyl-5-amino-2-chloro-4-fluorobenzamide are dissolved in 200 ml of pyridine and the solution is cooled to 0° C. 30.4 g of ethyl chloroformate are added dropwise at 0° C. while stirring and thereafter the reaction mixture is stirred for 14 hours. The mixture is poured into 1 liter of ice-water, the aqueous mixture is extracted three times with 250 ml of ethyl acetate each time, the combined organic phases are washed to neutrality, dried over anhydrous sodium sulphate and the solvent is evaporated off. The product is crystallized from diethyl ether. In this manner there is obtained ethyl 4-chloro-2-fluoro-5-(N-methoxy-N-methylcarbamoyl)-carbanilate, m.p. 121° C., used as the starting material in Example 1.

Workup

  1. stirringthe reaction mixture is stirred for 14 hours
  2. extractionthe aqueous mixture is extracted three times with 250 ml of ethyl acetate each time
  3. washthe combined organic phases are washed to neutrality
  4. dry with materialdried over anhydrous sodium sulphate
  5. customthe solvent is evaporated off
  6. customThe product is crystallized from diethyl ether

Sources & evidence

ORD record
ord-41428142b5884442b205a3ac97572918
Source dataset
uspto-grants-1991_05
Patent number
US05017211

Reaction notes

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