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Ammonia → 1-Trityl-4-(2,2-diphenylethyl)-5-methylimidazole

HRID 649232
Notes
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Reaction equation

HRID 649232 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 110469654-(Chloromethyl)-5-methyl-1-trityl-1H-imidazole

Product 1

HCID 147363691-Trityl-4-(2,2-diphenylethyl)-5-methylimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. extractionthe mixture is extracted with ether
  2. washThe organic phase is washed with water
  3. dry with materialdried over potassium carbonate
  4. customevaporated under reduced pressure
  5. additionThe residual oil is dispersed in heptane
  6. temperaturecooled with an ice bath
  7. customthe precipitation of a yellow solid which
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes