Water → 1-(triphenylmethyl)-1H-imidazole-4-carbaldehyde
Reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.CCN(CC)CC.O>CS(C)=O>[C:21]1([C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:6]2[CH:7]=[C:3]([CH:2]=[O:1])[N:4]=[CH:5]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
The product from Step 8.a. (2.04 g, 6.00 mmol) was suspended in DMSO (10.0 ml) and Et3N (3.34 ml, 24.0 mmol) and SO3-pyridine complex (2.39 g, 15.0 mmol) were added at room temperature. The mixture was warmed at about 110° C. for about 1 hour and then allowed to cool. The mixture was poured into 150 ml H2O and the product was filtered off. The residue was treated with saturated NaHCO3 solution (50 ml) and extracted 2×100 ml CH2Cl2. The combined CH2Cl2 layers were washed with 5% citric acid solution (100 ml), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was crystallized from MeOH and H2O. Yield=1.08 g (53%).
Workup
- temperatureto cool
- filtrationthe product was filtered off
- additionThe residue was treated with saturated NaHCO3 solution (50 ml)
- extractionextracted 2×100 ml CH2Cl2
- washThe combined CH2Cl2 layers were washed with 5% citric acid solution (100 ml)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was crystallized from MeOH and H2O
Sources & evidence
- ORD record
- ord-2f7bebf242b043158f96d189fb9a9a5c
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07361656B2
Reaction notes
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