4-Fluorobenzohydrazide → HCID 178465640, compound

HRID 1951635Notes

Reaction equation

HRID 1951635 reaction equation
[OH:1][C@H:2]([C:9]1[N:10]=[C:11]([C:14](=O)[CH3:15])[NH:12][CH:13]=1)[C@H:3]([OH:8])[C@H:4]([OH:7])[CH2:5][OH:6].[F:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([NH:24][NH2:25])=[O:23])=[CH:20][CH:19]=1>C(O)C.O.Cl>[F:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([NH:24]/[N:25]=[C:14](/[C:11]2[NH:12][CH:13]=[C:9]([C@@H:2]([OH:1])[C@H:3]([OH:8])[C@H:4]([OH:7])[CH2:5][OH:6])[N:10]=2)\[CH3:15])=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 99724-FluorobenzohydrazideHCID 178467425HCID 178467425, compound

Product 1

HCID 178465640HCID 178465640, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

1-[4-((1R,2S,3R)-1,2,3,4-Tetrahydroxy-butyl)-1H-imidazol-2-yl]-ethanone (172 mg, 0.74 mmol) was suspended in ethanol (4 ml) and water (1 ml). 4-fluorobenzoic acid hydrazide (131 mg, 0.85 mmol, 1.1 eq.) and hydrochloric acid (one drop, 12 N) were added, and the suspension was stirred at 55° C. for 48 hours. LCMS analysis indicated the formation of the product and the absence of starting material. The reaction mixture was cooled to room temperature, and partially concentrated in vacuo. The resulting white precipitate was collected and washed with ethanol to yield the product, as one apparent isomer, as a white solid: 97 mg (35%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationpartially concentrated in vacuo
  3. customThe resulting white precipitate was collected
  4. washwashed with ethanol
  5. customto yield the product

Sources & evidence

ORD record
ord-c5f69ce9b1194f5292a261aab4d27a27
Source dataset
uspto-grants-2013_03
Patent number
US08404732B2

Reaction notes

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