Hydrochloric Acid → Ethyl [2-(2-chloro-4-fluoro-5-ethoxycarbonylaminophenoxy)phenoxy]acetate

HRID 433728Notes

Reaction equation

HRID 433728 reaction equation
[NH2:1][C:2]1[C:3]([F:23])=[CH:4][C:5]([Cl:22])=[C:6]([CH:21]=1)[O:7][C:8]1[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=1[O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26].O1CCCC1.Cl>N1C=CC=CC=1>[Cl:22][C:5]1[CH:4]=[C:3]([F:23])[C:2]([NH:1][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][C:6]=1[O:7][C:8]1[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=1[O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 86584267HCID 86584267, compound

Product 1

HCID 17812347Ethyl [2-(2-chloro-4-fluoro-5-ethoxycarbonylaminophenoxy)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a mixture of ethyl [2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetate [Intermediate compound A3-23], ethyl chloroformate and tetrahydrofuran is added dropwise pyridine, and the mixture is stirred at room temperature. Dilute hydrochloric acid is added to the reaction solution, and this is extracted with ethyl acetate. The organic layer is washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated to obtain ethyl [2-(2-chloro-4-fluoro-5-ethoxycarbonylaminophenoxy)phenoxy]acetate [Intermediate compound A8-23].

Workup

  1. extractionthis is extracted with ethyl acetate
  2. washThe organic layer is washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-131d216d078f4668a46e525c58d7bd00
Source dataset
uspto-grants-2003_12
Patent number
US06667413B2

Reaction notes

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