Oxalic Acid → 2-(1-Trityl-1h-imidazol-4-yl)-benzylamine oxalate salt

HRID 1795259Notes

Reaction equation

HRID 1795259 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH2:27][NH2:28])[N:22]=[CH:21]1)([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:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35].CCCCCC>O1CCCC1>[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35].[C:1]([N:20]1[CH:24]=[C:23]([C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH2:27][NH2:28])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 8058HexaneHCID 113274852-(1-trityl-1H-imidazol-4-yl)-benzylamine

Product 1

HCID 221851452-(1-Trityl-1h-imidazol-4-yl)-benzylamine oxalate salt

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The crude 2-(1-trityl-1H-imidazol-4-yl)-benzylamine (66.1 g, 159 mmol) was dissolved in tetrahydrofuran (420 ml). Solid oxalic acid (14.3 g, 159 mmol) was added to the solution while stirring. This mixture was stirred at room temperature for 15 min and then added dropwise to stirring hexane (2000 ml). Tetrahydrofuran (100 ml) was used to rinse the glassware. A yellow solid precipitated. The mixture was stirred for an additional 20 min and the product was isolated by filtration. The solid was rinsed with 4:1 hexane:tetrahydrofuran (625 ml) and dried in a vacuum oven at ˜45° C. with an air purge for 18 h to afford 2-(1-trityl-1H-imidazol-4-yl)-benzylamine oxalate salt; MS (ES+) M+1 416.6 for C29H25N3.

Workup

  1. stirringThis mixture was stirred at room temperature for 15 min
  2. additionadded dropwise
  3. washto rinse the glassware
  4. customA yellow solid precipitated
  5. stirringThe mixture was stirred for an additional 20 min
  6. customthe product was isolated by filtration
  7. washThe solid was rinsed with 4:1 hexane
  8. dry with materialtetrahydrofuran (625 ml) and dried in a vacuum oven at ˜45° C. with an air
  9. custompurge for 18 h

Sources & evidence

ORD record
ord-abcb3b73f49b44449652b1098bdef782
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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