Pyridine → HCID 178527120, compound

HRID 330276Notes

Reaction equation

HRID 330276 reaction equation
[S:1](Cl)(Cl)=[O:2].[OH:5][N:6]=[C:7]([NH2:19])[CH2:8][C:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1.N1C=CC=CC=1>C(Cl)Cl>[CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:17][CH2:18][C:9]=1[CH2:8][C:7]1[NH:19][S:1](=[O:2])[O:5][N:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 53673050HCID 53673050, compound

Product 1

HCID 178527120HCID 178527120, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (2.55 mL, 0.035 mol) was added dropwise to a mixture of N'-hydroxy-(3,4-dihydro-2-naphthalenyl)ethanimidamide (6.5 g, 0.032 mol) and pyridine (5.18 mL, 0.064 mol) in dry CH2Cl2 (100 mL) at 0° C. After the addition, the reaction mixture was concentrated under reduced pressure, placed in an ice bath, diluted with water (50 mL), extracted with ether (3×50 mL), filtered, dried (MgSO4), and concentrated under reduced pressure to give a red brown solid. The solid was triturated three times with ether (50 mL) and recrystallized from ether (75 mL) to yield 1.14 g (14.4%) of pure product as tan crystals, m.p. 118°-120.5° C.

Workup

  1. additionAfter the addition
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customplaced in an ice bath
  4. additiondiluted with water (50 mL)
  5. extractionextracted with ether (3×50 mL)
  6. filtrationfiltered
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customto give a red brown solid
  10. customThe solid was triturated three times with ether (50 mL)
  11. customrecrystallized from ether (75 mL)

Sources & evidence

ORD record
ord-25b75f42b64d441cbc2e0dcf19914ed1
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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