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Triethylamine → HCID 21705605, compound

HRID 1596059
Notes
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Reaction equation

HRID 1596059 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([OH:29])(=[O:1])=[O:28].[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 138793714'-(2-Hydroxyethoxy)[1,1'-biphenyl]-4-carbonitrile

Product 1

HCID 21705605HCID 21705605, compoundYield 175.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of example 14A (150 mg, 0.63 mmol) in 6 mL CH2Cl2 at 0° C. was added triethylamine (127 mg, 1.26 mmol, 2 eq.) followed by methanesulfonyl chloride (108 mg, 0.94 mmol, 1.5 eq.). After stirring at ambient temperature for 4 h, the reaction mixture was concentrated and purified on silica gel with 25% EtOAc/hexanes to provide 185 mg (92%) of the desired compound as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified on silica gel with 25% EtOAc/hexanes

Sources & evidence

ORD record
ord-38e37247a1044d0d92a619b9094c6a12
Source dataset
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06288261B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes