Hydrochloric Acid → HCID 19041628, compound

HRID 1684002Notes

Reaction equation

HRID 1684002 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]([C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)N)=[CH:4][CH:3]=1.O=[C:19]([CH3:32])[CH2:20][CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25].Cl>O1CCOCC1>[Br:15][C:12]1[CH:11]=[C:10]2[C:9](=[CH:14][CH:13]=1)[N:7]([CH2:6][C:5]1[CH:16]=[CH:17][C:2]([Br:1])=[CH:3][CH:4]=1)[C:19]([CH3:32])=[C:20]2[CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3237420methyl 2-(3-oxobutyl)benzoateHCID 19041651HCID 19041651, compound

Product 1

HCID 19041628HCID 19041628, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
70 °C

Procedure

To a room temperature solution of N-(4-bromobenzyl)-N-(4-bromophenyl)hydrazine (335 mg, 0.941 mmol) and methyl 2-(3-oxobutyl)benzoate (202 mg, 0.98 mmol) in 6 mL dioxane was added 1.5 mL of 4N HCl solution in dioxane. Heated to 70° C. for 16 h, then concentrated, the residue was partitioned between EtOAc and water, then washed with 1M HCl and brine. Dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography (40% CH2Cl2 /Hexanes) provided 195 mg of the title compound.

Workup

  1. concentrationconcentrated
  2. customthe residue was partitioned between EtOAc and water
  3. washwashed with 1M HCl and brine
  4. dry with materialDried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (40% CH2Cl2 /Hexanes)

Sources & evidence

ORD record
ord-176559faafca41fa9d7a3dcb5301e3d1
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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