Hydrochloric Acid → HCID 22451126, compound

HRID 2185626Notes

Reaction equation

HRID 2185626 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([F:17])[C:14]([NH2:18])=[CH:13][C:3]=1[O:4][C:5]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6]1.CN(C)C1C=CC=CC=1.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30].Cl>C1COCC1>[Cl:1][C:2]1[CH:16]=[C:15]([F:17])[C:14]([NH:18][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:13][C:3]=1[O:4][C:5]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 10928Ethyl chloroformateHCID 22451125HCID 22451125, compound

Product 1

HCID 22451126HCID 22451126, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The obtained ethyl 1-(2-chloro-4-fluoro-5-amino-phenoxy)cyclopropanecarboxylate (1 equivalent) and dimethylaniline (1 equivalent) are added to THF and ethyl chloroformate (1 equivalent) is gradually added in drops thereto. After completion of addition, to the reaction solution is added aqueous diluted hydrochloric acid and the mixture is extracted with ethyl acetate. After concentrating the organic layer, the residue is subjected to chromatography to give ethyl 1-(2-chloro-4-fluoro-5-ethoxycarbonylaminophenoxy)cyclo-propanecarboxylate.

Workup

  1. additionis gradually added in drops
  2. additionAfter completion of addition
  3. extractionthe mixture is extracted with ethyl acetate
  4. concentrationAfter concentrating the organic layer

Sources & evidence

ORD record
ord-1f04c20db8c449c1b6085289b24ebc99
Source dataset
uspto-grants-2002_06
Patent number
US06403534B1

Reaction notes

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