Sodium Hydroxide → 2-(1-Trityl-1H-imidazol-4-yl)-ethylamine

HRID 240296Notes

Reaction equation

HRID 240296 reaction equation
FC(F)(F)C([NH:5][CH2:6][CH2:7][C:8]1[N:9]=[CH:10][N:11]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=1)=O.[OH-].[Na+]>O1CCCC1.CO.O>[C:13]([N:11]1[CH:12]=[C:8]([CH2:7][CH2:6][NH2:5])[N:9]=[CH:10]1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 110377171-(Triphenylmethyl)-4-[2-(trifluoroacetamido)-1-ethyl]imidazole

Product 1

HCID 6183402-(1-Trityl-1H-imidazol-4-yl)-ethylamineYield 82%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above amide (45.54 g; 0.101 mmol) was dissolved in tetrahydrofuran (1000 mL) and methanol (1200 mL). A solution of sodium hydroxide (20.26 g; 0.507 mol) in water (500 mL) was added. Mixture was stirred for 2 hrs at room temperature and then it was concentrated in vacuo. The residue was separated between chloroform (1200 mL) and water (800 mL). Aqueous layer was extracted with chloroform (3×400 mL). Organic layers were combined and dried over anhydrous magnesium sulfate. Evaporation of the solvent yielded brown oil, which was dried for 3 days in vacuo to give the title product as beige solid.

Workup

  1. concentrationit was concentrated in vacuo
  2. customThe residue was separated between chloroform (1200 mL) and water (800 mL)
  3. extractionAqueous layer was extracted with chloroform (3×400 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent
  6. customyielded brown oil, which
  7. customwas dried for 3 days in vacuo

Sources & evidence

ORD record
ord-dccd7eb56b6d4d038577f89b8e45b720
Source dataset
uspto-grants-2014_02
Patent number
US08648041B2

Reaction notes

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