Acetic Acid → HCID 21697022, compound

HRID 379050Notes

Reaction equation

HRID 379050 reaction equation
FC(F)(F)[C:3](O)=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]([CH:34]=[CH:35][CH:36]=1)[O:12][C:13]1[CH:20]=[C:19]([CH:21]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16].[OH-].[K+].C=O.C(O)(=O)C>C(#N)C.CO>[ClH:8].[Cl:8][C:9]1[CH:10]=[C:11]([CH:34]=[CH:35][CH:36]=1)[O:12][C:13]1[CH:20]=[C:19]([C:21]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)([N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)[CH2:3][OH:4])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 21697031HCID 21697031, compound

Product 1

HCID 21697022HCID 21697022, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(3-chloro-phenoxy)-4-[(4-chloro-phenyl)-imidazol-1-yl-methyl]-benzonitrile trifluoroacetate (0.065 g, 0.122 mmol) in acetonitrile (5 mL) was added 1M KOH (0.5 mL) (pH=9-10) and 37% aqueous formaldehyde (0.14 mL) After stirring for 18 hr the mixture was adjusted to pH=3 with acetic acid, diluted with CH3OH (3 mL) and purified on prep HPLC. The TFA salt was converted to the HCl salt to obtain the title compound.

Workup

  1. custompurified on prep HPLC

Sources & evidence

ORD record
ord-b689b46dcd81449fac857e70e9f30fbb
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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