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Hydrochloric Acid → HCID 89444221, compound

HRID 1771725
Notes
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Reaction equation

HRID 1771725 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:16][NH:17][C:18]2[C:19]([F:32])=[C:20]([CH:28]=[CH:29][C:30]=2[F:31])[O:21][CH2:22][C:23]([O:25]CC)=[O:24])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[CH:8]=1)#[N:2].C([O-])([O-])=[O:34].[K+].[K+].OO.Cl>CS(C)=O.O>[C:1]([C:3]1[CH:4]=[C:5]([CH2:16][NH:17][C:18]2[C:19]([F:32])=[C:20]([CH:28]=[CH:29][C:30]=2[F:31])[O:21][CH2:22][C:23]([OH:25])=[O:24])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[CH:8]=1)(=[O:34])[NH2:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 89443820HCID 89443820, compound

Product 1

HCID 89444221HCID 89444221, compoundYield 46.5%

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent

Procedure

To a mixture of ethyl 2-[3-[[3-cyano-5-(3-fluorophenyl)phenyl]methylamino]-2,4-difluoro-phenoxy]acetate (see example 24) (200 mg, 0.45 mmol, 1 eq) and K2CO3 (310 mg, 2.3 mmol, 5 eq) in DMSO (10 mL) at 40° C. was added H2O2 (30% aqueous solution, 10 mL) dropwise. The mixture was stirred for 20 min then cooled to room temperature. Water was added, and the reaction neutralised by addition of diluted HCl. The solid precipitate that formed was collected by filtration, washed with water and dried to give the title compound as white solid (90 mg, 46%).

Workup

  1. customThe solid precipitate that formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-0ff5f1488c264f43a7cb97dc591ec4b5
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249085B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes