Hydrochloric Acid → HCID 22058784, compound

HRID 1828826Notes

Reaction equation

HRID 1828826 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH3:26])[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][C:14]=2[Cl:25])[C:6]=1/[CH:7]=[CH:8]/[C:9]([OH:11])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[Na].[CH:40](/[S:45]([NH2:48])(=[O:47])=[O:46])=[CH:41]\[CH2:42][CH2:43][CH3:44].Cl>CN(C)C=O.O>[Cl:1][C:2]1[N:3]=[C:4]([CH3:26])[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][C:14]=2[Cl:25])[C:6]=1/[CH:7]=[CH:8]/[C:9]([NH:48][S:45](/[CH:40]=[CH:41]/[CH2:42][CH2:43][CH3:44])(=[O:47])=[O:46])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 22058598HCID 22058598, compoundHCID 86760102HCID 86760102, compound

Product 1

HCID 22058784HCID 22058784, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(E)-3-(4-Chloro-1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methylimidazol-5-yl)-2-propenic acid (150 mg) was dissolved in N,N-dimethylformamide (1.5 ml) and carbonyldiimidazole was added. The mixture was stirred at room temperature for 3 hr. To the reaction mixture was added (E)-1-penten-1-ylsulfonamide sodium salt (97 mg), and the mixture was stirred at room temperature for 3 hr and left standing for one day. The reaction mixture was diluted with water (1.5 ml) and adjusted to pH 4 with 1N hydrochloric acid under ice-cooling. The precipitated powder was collected by filtration and washed with water. The resulting white powder was suspended in ethanol (0.75 ml) and heated. The mixture was stirred at room temperature for 30 min. The precipitate was collected by filtration, washed with ethanol and dissolved in N,N-dimethylformamide (0.75 ml) at 80° C. Water (0.25 ml) was added at the same temperature and the mixture was stirred at room temperature for 1 hr. The precipitated crystals were collected by filtration, washed with N,N-dimethylformamide—water (1:1) and then with water to give (E)-3-(4-chloro-1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methylimidazol-5-yl)-N-((E)-1-penten-1-ylsulfonyl)-2-propenamide (160 mg) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. waitleft
  3. waitstanding for one day
  4. temperaturecooling
  5. filtrationThe precipitated powder was collected by filtration
  6. washwashed with water
  7. temperatureheated
  8. stirringThe mixture was stirred at room temperature for 30 min
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with ethanol
  11. dissolutiondissolved in N,N-dimethylformamide (0.75 ml) at 80° C
  12. additionWater (0.25 ml) was added at the same temperature
  13. stirringthe mixture was stirred at room temperature for 1 hr
  14. filtrationThe precipitated crystals were collected by filtration
  15. washwashed with N,N-dimethylformamide—water (1:1)

Sources & evidence

ORD record
ord-5e0b432d73d748f9add799cf102d8f79
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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