Ammonium Chloride → 6-(hydroxy(1-trityl-1H-imidazol-4-yl)methyl)-N-methyl-2-naphthamide

HRID 922714Notes

Reaction equation

HRID 922714 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:14][CH3:15])=[O:13])[CH:6]=[CH:5]2.CCCCCCC.C([Mg]CCCC)CCC.CCCCCC.C([Li])CCC.[C:43]([N:62]1[CH:66]=[C:65]([CH:67]=[O:68])[N:64]=[CH:63]1)([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.[Cl-].[NH4+]>O1CCCC1>[OH:68][CH:67]([C:65]1[N:64]=[CH:63][N:62]([C:43]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:66]=1)[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:14][CH3:15])=[O:13])[CH:6]=[CH:5]2

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 218796286-bromo-N-methyl-2-naphtamideHCID 178418244HCID 178418244, compoundHCID 178443322HCID 178443322, compound

Product 1

HCID 574658056-(hydroxy(1-trityl-1H-imidazol-4-yl)methyl)-N-methyl-2-naphthamideYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-13 °C

Procedure

Under a nitrogen atmosphere, 6-bromo-N-methyl-2-naphthamide (1.0 g, 3.79 mmol) was added to tetrahydrofuran (25 mL), and then 1.0 mol/L dibutylmagnesium heptane solution (2.0 mL) was added dropwise thereto at room temperature. The obtained solution was cooled to −13° C., 1.6 mol/L n-butyllithium hexane solution (2.6 mL) was added dropwise thereto, and the mixture was stirred at the same temperature for 1.5 hr. A solution of 1-trityl-4-formyl-1H-imidazole (1.4 g, 4.2 mmol) in tetrahydrofuran (15 mL) was added dropwise to the reaction mixture at −11° C., and the mixture was stirred at the same temperature for 5 hr. The reaction mixture was allowed to warm to 6° C. over 2.5 hr, and 20 w/v % aqueous ammonium chloride solution (30 mL) was added dropwise thereto. The organic layer was separated, and quantified to give 6-[hydroxy(1-trityl-1H-imidazol-4-yl)methyl]-N-methyl-2-naphthamide (1.2 g, 2.24 mmol). yield 71%.

Workup

  1. customat room temperature
  2. stirringthe mixture was stirred at the same temperature for 5 hr
  3. temperatureto warm to 6° C. over 2.5 hr
  4. customThe organic layer was separated

Sources & evidence

ORD record
ord-8e561e6e5c384917ad3570fb85c9437d
Source dataset
uspto-grants-2016_03
Patent number
US09278938B2

Reaction notes

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