1,4-Dioxane → HCID 178488262, compound

HRID 869392Notes

Reaction equation

HRID 869392 reaction equation
[Cl:1][C:2]1[C:7]2[C:8]3[NH:9][CH:10]([C:16]4[N:17]=[C:18]([CH:21]([CH3:23])[CH3:22])[S:19][CH:20]=4)[CH2:11][C:12](=[O:15])[C:13]=3[O:14][C:6]=2[CH:5]=[CH:4][C:3]=1[O:24][CH3:25].O1CCOCC1>O>[OH:15][C:12]1[CH:11]=[C:10]([C:16]2[N:17]=[C:18]([CH:21]([CH3:23])[CH3:22])[S:19][CH:20]=2)[N:9]=[C:8]2[C:7]3[C:2]([Cl:1])=[C:3]([O:24][CH3:25])[CH:4]=[CH:5][C:6]=3[O:14][C:13]=12

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 86722240HCID 86722240, compound

Product 1

HCID 178488262HCID 178488262, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10B (10.3 g, 27.33 mmol, crude) and FeCl3.6H2O (33.04 g, 164.0 mmol, 6 eq) was added to 1,4-dioxane (300 mL) The mixture was refluxed for 16 hours. TLC monitored the reaction. After the reaction completed, the reaction mixture was cooled to room temperature and poured into water (300 mL), extracted with ethyl acetate and concentrated to give a crude product 10C (8.75 g), which was used for the next step directly.

Workup

  1. temperaturewas refluxed for 16 hours
  2. customthe reaction
  3. extractionextracted with ethyl acetate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c6d8994519104d73b8fc119851e8f142
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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