Ammonia → 1-Trityl-4-[2-phenyl-2-(4-pyridinyl)ethyl]-imidazole

HRID 1639033Notes

Reaction equation

HRID 1639033 reaction equation
N.[Na].[C:3]1([CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:16]([N:35]1[CH:39]=[C:38]([CH2:40]Cl)[N:37]=[CH:36]1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCOCC.C1COCC1>[C:16]([N:35]1[CH:39]=[C:38]([CH2:40][CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)[N:37]=[CH:36]1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 222Ammonia3×HCID 164584-BenzylpyridineHCID 27631764-(Chloromethyl)-1-trityl-1H-imidazoleHCID 5360545Sodium2×

Product 1

HCID 146253061-Trityl-4-[2-phenyl-2-(4-pyridinyl)ethyl]-imidazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

Under nitrogen atmosphere a 100 ml flask was charged with 50 ml liquid ammonia, a small piece of sodium and a few crystals of Fe(NO3)3. Then about 0.25 g (11 mmol) sodium metal was added and the mixture was stirred at ca. -70° C. for 0.5 hours. Then, under stirring, and at about -70° C. 1.69 g (10 mmoles) of phenyl-(4-pyridinyl)methane dissolved in 5 ml anhydrous ether are added in 10 minutes. After stirring for 0.5 hours the mixture was allowed to warm up to the boiling temperature of ammonia and 3.21 g (9 mmoles) of (3) dissolved in 20 ml anhydrous THF was added dropwise. The mixture was allowed to warm up to room temperature while ammonia evaporated. To the residue 30 ml water was added and the mixture was extracted with methylene chloride. Then the methylene chloride was evaporated from the dried, combined solutions yielding crude derivative (4) used as such in the next stage.

Workup

  1. stirringThen, under stirring
  2. customat about -70° C
  3. additionare added in 10 minutes
  4. stirringAfter stirring for 0.5 hours the mixture
  5. additionwas added dropwise
  6. customevaporated
  7. additionTo the residue 30 ml water was added
  8. extractionthe mixture was extracted with methylene chloride
  9. customThen the methylene chloride was evaporated from the dried

Sources & evidence

ORD record
ord-1d19b8c130bb44a8b86041eda59383c8
Source dataset
uspto-grants-1989_11
Patent number
US04882343

Reaction notes

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