Hydrochloric Acid → N-methyl-6-((trityl-1H-imidazol-4-yl)carbonyl)-2-naphthamide

HRID 922717Notes

Reaction equation

HRID 922717 reaction equation
[OH:1][CH:2]([C:17]1[N:18]=[CH:19][N:20]([C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=1)[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([NH:15][CH3:16])=[O:14])[CH:7]=[CH:6]2.CN(C)C(=O)C.[H-].[Na+].Cl>O>[CH3:16][NH:15][C:13]([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:2]([C:17]3[N:18]=[CH:19][N:20]([C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:21]=3)=[O:1])[CH:4]=2)[CH:9]=1)=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 574658056-(hydroxy(1-trityl-1H-imidazol-4-yl)methyl)-N-methyl-2-naphthamide

Product 1

HCID 18769037N-methyl-6-((trityl-1H-imidazol-4-yl)carbonyl)-2-naphthamideYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, 6-[hydroxy(1-trityl-1H-imidazol-4-yl)methyl]-N-methyl-2-naphthamide (1.0 g, 1.91 mmol) was added to N,N-dimethylacetamide (50 mL), and then sodium hydride (oil, 0.15 g, 3.85 mmol) was added at room temperature, and the mixture was stirred at the same temperature for about 60 hr. To the reaction mixture were added dropwise water (50 mL) and 1 mol/L hydrochloric acid (5 mL) at room temperature, and the mixture was stirred at the same temperature for 45 min. Then, the reaction mixture was cooled to 0° C., and stirred for 2 hr. The crystals were collected by filtration, and washed with water (30 mL). The obtained wet crystals were dried under reduced pressure to give N-methyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthamide (0.89 g, 1.71 mmol). yield 90%.

Workup

  1. stirringthe mixture was stirred at the same temperature for 45 min
  2. stirringstirred for 2 hr
  3. filtrationThe crystals were collected by filtration
  4. washwashed with water (30 mL)
  5. customThe obtained wet crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-0f76d936b59c498b9b7a69e483c18b3e
Source dataset
uspto-grants-2016_03
Patent number
US09278938B2

Reaction notes

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