Hydrochloric Acid → HCID 12832382, compound

HRID 1995234Notes

Reaction equation

HRID 1995234 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([SH:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[H-].[Na+].[F:25][C:26]([F:35])([F:34])[C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)N.N([O-])=O.[Na+].Cl>CN(C)C=O.[Cu]>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[C:11]([S:22][C:32]3[CH:31]=[CH:29][CH:28]=[C:27]([C:26]([F:35])([F:34])[F:25])[CH:33]=3)[NH:10][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 73753-(Trifluoromethyl)anilineHCID 24758Sodium hydrideHCID 23668193Sodium NitriteHCID 178489021HCID 178489021, compound

Product 1

HCID 12832382HCID 12832382, compoundYield 35.8%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

Under the conditions of Example 85, 6.25 g of 4,5-bis(4-methoxyphenyl)-2-mercaptoimidazole is reacted in 150 ml of dimethylformamide in the presence of a pinch of powdered copper with 0.60 g of sodium hydride (80% in oil) and a diazonium salt solution prepared from 3.26 g of 3-trifluoromethylaniline (99%), 1.38 g of sodium nitrite, as well as 10 ml of 6 N hydrochloric acid. Chromatography according to Example 85 yields 3.27 g of 4,5-bis(4-methoxyphenyl)-2-(3-trifluoromethylphenylthio)imidazole as an amorphous foam.

Sources & evidence

ORD record
ord-0ed25dedd9844059872399df17a2baf0
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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