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Ethyl Acetate → 2-Chloro-4-[4-(2-methoxy-ethoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile

HRID 2233594
Notes
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Reaction equation

HRID 2233594 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[C:31]#[N:32])[O:5][CH2:6][C:7]1[S:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH2:22][O:23]S(C)(=O)=O.[H-].[Na+].[C:35]([O:38][CH2:39]C)(=O)[CH3:36]>COCCO>[Cl:1][C:2]1[CH:3]=[C:4]([O:5][CH2:6][C:7]2[S:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH2:22][O:23][CH2:36][CH2:35][O:38][CH3:39])[CH:28]=[CH:29][C:30]=1[C:31]#[N:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 59296164Methanesulfonic acid 5-(3-chloro-4-cyano-phenoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethyl ester

Product 1

HCID 592962052-Chloro-4-[4-(2-methoxy-ethoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile

Reagents, catalysts & solvents 1

HCID 8019
2-Methoxyethanol
Solvent

Conditions

Temperature
50 °C

Procedure

120 mg Methanesulfonic acid 5-(3-chloro-4-cyano-phenoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethyl ester were dissolved in 5 ml 2-methoxyethanol. 10.0 mg sodium hydride were added and the mixture stirred at 50° C. for one hour. The reaction mixture was diluted by addition of 50 ml ethyl acetate, washed with brine then dried over MgSO4. The solvent was removed in vacuo and the residue purified by RP-HPLC to provide 30 mg of 2-Chloro-4-[4-(2-methoxy-ethoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile as lyophilisate.

Workup

  1. washwashed with brine
  2. dry with materialthen dried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by RP-HPLC

Sources & evidence

ORD record
ord-34be27bcb09b44068558526d464502d5
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709509B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes