3-Chlorobenzohydrazide → HCID 178465636, compound

HRID 1169862Notes

Reaction equation

HRID 1169862 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].[Cl:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([NH:23][NH2:24])=[O:22]>C(O)C.O.Cl>[Cl:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([NH:23][N:24]=[C:14]([C:11]1[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]=1)[CH3:15])=[O:22]

Participants

6

Reactant 2

HCID 742893-ChlorobenzohydrazideHCID 178467425HCID 178467425, compound

Product 1

HCID 178465636HCID 178465636, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1-[4-((1R,2S,3R)-1,2,3,4-Tetrahydroxy-butyl)-1H-imidazol-2-yl]-ethanone (194 mg, 0.84 mmol) was suspended in ethanol (4 ml) and water (1 ml). 3-Chlorobenzoic acid hydrazide (170 mg, 1.0 mmol, 1.2 eq.) and hydrochloric acid (one drop, 12 N) were added, and the suspension was stirred at 50° 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 a ˜3:1 E:Z mixture, as a white solid: 108 mg (33%).

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-42720a87086d498ca0d204ac9dc6d1c9
Source dataset
uspto-grants-2010_11
Patent number
US07825150B2

Reaction notes

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