Hydrochloric Acid → Methyl [2-(2-chloro-4-fluoro-5-methoxycarbonylaminophenoxy)phenoxy]acetate

HRID 433722Notes

Reaction equation

HRID 433722 reaction equation
[NH2:1][C:2]1[C:3]([F:22])=[CH:4][C:5]([Cl:21])=[C:6]([CH:20]=1)[O:7][C:8]1[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=1[O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].Cl[C:24]([O:26][CH3:27])=[O:25].O1CCCC1.Cl>N1C=CC=CC=1>[Cl:21][C:5]1[CH:4]=[C:3]([F:22])[C:2]([NH:1][C:24]([O:26][CH3:27])=[O:25])=[CH:20][C:6]=1[O:7][C:8]1[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=1[O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 8028TetrahydrofuranHCID 23380315Methyl [2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetate

Product 1

HCID 86584265Methyl [2-(2-chloro-4-fluoro-5-methoxycarbonylaminophenoxy)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a mixture of methyl [2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetate [Intermediate compound A3-22], methyl 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 methyl [2-(2-chloro-4-fluoro-5-methoxycarbonylaminophenoxy)phenoxy]acetate [Intermediate compound A9-22].

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-ef274cf11d504a32a54c037f5fc9dbdb
Source dataset
uspto-grants-2003_12
Patent number
US06667413B2

Reaction notes

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