Hydrochloric Acid → HCID 54712961, compound

HRID 965174Notes

Reaction equation

HRID 965174 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:16])[CH:8]=1)=[O:5])#[N:2].[H-].[Na+].[C:19](N1C=CN=C1)(=[O:21])[CH3:20].Cl>O1CCCC1.C(O)(=O)C>[CH3:16][C:9]1[CH:8]=[C:7]([NH:6][C:4](=[O:5])/[C:3](/[C:1]#[N:2])=[C:19](\[OH:21])/[CH3:20])[CH:12]=[CH:11][C:10]=1[N+:13]([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 24758Sodium hydrideHCID 19076040HCID 19076040, compound

Product 1

HCID 54712961HCID 54712961, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

2-Cyano-N-(3-methyl-4-nitrophenyl)acetamide (0.61 g; 2.8 mmol) is dissolved in tetrahydrofuran (30 ml) and sodium hydride (80% strength dispersion in oil; 0.21 g; 7 mmol) is added. The mixture is stirred at 25° C. for 15 minutes and 1-acetylimidazole (0.46 g; 4.2 mmol) is added dropwise over the course of 5 minutes and the mixture is stirred for a further 15 minutes. 2 ml of glacial acetic acid are added and the mixture is stirred at 25° C. for 1 hour and then poured into ice-cold water (100 ml). The pH of the solution is then adjusted to 1 using concentrated hydrochloric acid, and the precipitate is filtered, washed with water and brought to dryness under reduced pressure. N-(3-Methyl-4-nitrophenyl)-2-cyano-3-hydroxycrotonamide is thus obtained.

Workup

  1. stirringthe mixture is stirred for a further 15 minutes
  2. stirringthe mixture is stirred at 25° C. for 1 hour
  3. filtrationthe precipitate is filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-78fcc7d80ae14e8fb17b1fbee8396d66
Source dataset
uspto-grants-1998_06
Patent number
US05773470

Reaction notes

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