Ammonia → 4-(2,2-Diphenylethyl)-5-methyl-1-(triphenylmethyl)-1H-imidazole

HRID 649232Notes

Reaction equation

[C:1]([N:20]1[C:24]([CH3:25])=[C:23]([CH2:26]Cl)[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N.[Cl-].[NH4+]>C1COCC1>[C:1]([N:20]1[C:24]([CH3:25])=[C:23]([CH2:26][CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Then it is cooled again to -78° C. and a solution of 1-trityl-4-chloromethyl-5-methylimidazole 3 in 10 ml of anhydrous THF is added thereto. After stirring for an hour at -78° C. the reaction mixture is kept at -20° C. for 48 hours. Then 30 ml of an aqueous 10% ammonia solution saturated with ammonium chloride are added and the mixture is extracted with ether. The organic phase is washed with water, dried over potassium carbonate and evaporated under reduced pressure. The residual oil is dispersed in heptane and cooled with an ice bath. This causes the precipitation of a yellow solid which is recrystallised in isopropanol. The 1-trityl-4-(2,2-diphenyl ethyl)-5-methylimidazole 4 is so obtained in the form of a white solid.

Workup

extractionthe mixture is extracted with ether
washThe organic phase is washed with water
dry with materialdried over potassium carbonate
customevaporated under reduced pressure
additionThe residual oil is dispersed in heptane
temperaturecooled with an ice bath
customthe precipitation of a yellow solid which
customis recrystallised in isopropanol

Sources & evidence

ORD record: ord-ee9897a5094948d4ab077167d1246df4
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04738979

Reaction notes

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