Ethanol → 2-Amino-1-trityl-imidazole

HRID 1672089Notes

Reaction equation

HRID 1672089 reaction equation
[C:1]([N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[N:25]=CN(C)C)([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.C(O)C.NN>C(O)(=O)C>[C:1]([N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[NH2:25])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 673433701-Trityl-2-[(dimethylamino)methylene]aminoimidazole

Product 1

HCID 103589742-Amino-1-trityl-imidazoleYield 97.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To 3 (44.64 g, 117 mmol) was added reagent grade ethanol (1200 mL), glacial acetic acid (20.65 mL) and hydrazine (26 mL). The reaction mixture was stirred at 50° C. for 5 hrs. Solvent was removed and to the crude product was added methylene chloride (1,500 ml) and 1 N sodium hydroxide (67 ml) with stirring at room temperature for 15 minutes. The two resulting layers were separated and the organic layer was washed with brine (2×300 mL), dried over anhydrous sodium sulfate, filtered and solvent removed in vacuo to obtain 1-trityl-2-aminoimidazole, 4 (37.2 g, 97%). M.p. 196-199° C.

Workup

  1. customSolvent was removed and to the crude product
  2. additionwas added methylene chloride (1,500 ml) and 1 N sodium hydroxide (67 ml)
  3. stirringwith stirring at room temperature for 15 minutes
  4. customThe two resulting layers were separated
  5. washthe organic layer was washed with brine (2×300 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-7eca61ff51494db0b75ffef10103defd
Source dataset
uspto-grants-2011_08
Patent number
US07998462B2

Reaction notes

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