Tetrahydrofuran → HCID 22601356, compound

HRID 970930Notes

Reaction equation

HRID 970930 reaction equation
[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=O.[NH2:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1.C1COCC1>S(Cl)(Cl)=O>[Cl:11][C:7]1[CH:8]=[N:9][CH:10]=[C:2]([Cl:1])[C:3]=1[C:4]([NH:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1)=[O:6]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 693314-Aminobenzyl alcoholHCID 6057633,5-Dichloroisonicotinic acid

Product 1

HCID 22601356HCID 22601356, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 3,5-dichloroisonicotinic acid (128 mg, 0.667 mmol) in thionyl chloride (2 mL) was heated at reflux for 2 h, then concentrated. To the residue was added 4-aminobenzyl alcohol (123 mg, 0.999 mmol) and THF (2.2 mL), and the mixture was stirred at room temperature for 19 h. The mixture was filtered, and the filtrate was concentrated to give a yellow foam (125 mg, 63%). 1H NMR (CD3OD) δ 4.60 (s, 2H), 7.38 (d, 2H, J=8.7 Hz), 7.63 (d, 2H, J=8.4 Hz), 8.66 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationconcentrated
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5e0614d8ce714495818e9fa16fa86079
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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