Sulfuric Acid → HCID 11568047, compound

HRID 1067657Notes

Reaction equation

HRID 1067657 reaction equation
N1C=C(CCC(O)=O)N=C1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].[C:21]([CH2:26][CH2:27][CH2:28][C:29]1[N:30]=[CH:31][NH:32][CH:33]=1)([O:23][CH2:24][CH3:25])=[O:22].C(N(CC)CC)C.[C:41]1([C:47](Cl)([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C(O)C.O.CN(C)C=O>[C:41]1([C:47]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)([C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)[N:32]2[CH:33]=[C:29]([CH2:28][CH2:27][CH2:26][C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:30]=[CH:31]2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

10

Reactant 6

HCID 1118Sulfuric AcidHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178471275HCID 178471275, compound2×HCID 178525356HCID 178525356, compound

Product 1

HCID 11568047HCID 11568047, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a reaction flask equipped for hydrogenation, 10 g of urocanic acid (72.4 mmol) are dissolved in 200 ml of water. 1 g of Pd/C (10%) are added and hydrogenation is performed at 50° C. for 4 hours. The catalyst is filtered off and the water evaporated off, giving 3-(4-imidazolyl)propionic acid which appears in the form of a white powder (8.8 g; 86%); m.p.: 209-211° C. (3-Imidazol-4-yl)propionic acid (6 g, 42 mmol) is dissolved in absolute ethanol (204 ml), and a catalytic amount of concentrated sulphuric acid (2 ml) is added. The resulting mixture is heated to reflux for 16 hours. The solvent is evaporated off, which gives an oily residue which is dissolved in 45 ml of water. The solution is neutralized with sodium hydrogencarbonate, and 4-(3-carboethoxypropyl)-1H-imidazole is extracted with ethyl acetate; an oil (5.1 g; 72%) is obtained. The 4-(3-carboethoxypropyl)-1H-imidazole (5.4 g, 32 mmol) is dissolved in 4 ml of anhydrous dimethylformamide. 3.4 g of triethylamine (33.6 mmol) and 9.3 g of triphenylmethyl chloride (33.6 mmol) are added, and the mixture is stirred at room temperature under nitrogen for 4 hours. The mixture is poured onto crushed ice (60 g), which gives a white precipitate which is recrystallized from diethyl ether (9.2 g; 70%), giving 1-(triphenylmethyl)-4-(3-carboethoxypropyl)-1H-imidazole; m.p.: 134° C.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 16 hours
  3. customThe solvent is evaporated off
  4. customwhich gives an oily residue which
  5. extractionis extracted with ethyl acetate
  6. customan oil (5.1 g; 72%) is obtained
  7. additionThe mixture is poured
  8. customgives a white precipitate which
  9. customis recrystallized from diethyl ether (9.2 g; 70%)

Sources & evidence

ORD record
ord-e819e2900fdd41cab07410e670eb4144
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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