Pyridine → HCID 178527122, compound

HRID 330269Notes

Reaction equation

HRID 330269 reaction equation
[S:1](Cl)(Cl)=[O:2].[OH:5][N:6]=[C:7]([NH2:20])[CH2:8][C:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[Cl:19].N1C=CC=CC=1>C(Cl)Cl>[Cl:19][C: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:20][S:1](=[O:2])[O:5][N:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 54323149HCID 54323149, compound

Product 1

HCID 178527122HCID 178527122, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.55 mL, 7.5 mmol) was added dropwise to a mixture of N'-hydroxy-(1-chloro-3,4-dihydro-2-naphthalenyl)ethanimidamide (1.6 g, 6.8 mmol) and pyridine (1.10 mL, 13.6 mmol) in dry CH2Cl2 (25 mL) at 0° C. After the addition, the reaction was concentrated under reduced pressure, diluted with water (50 mL), and extracted with ether (3×50 mL). The organics were washed with brine, dried (MgSO4), and concentrated to obtain a black froth. The froth was chromatographed on silica gel (twice: eluant 4% MeOH/CH3Cl2 and eluant 2% MeOH/CH2Cl2) to yield 612 mg (32%) of an off-white solid, m.p. 90.5°-91.5° C.

Workup

  1. additionAfter the addition
  2. concentrationthe reaction was concentrated under reduced pressure
  3. additiondiluted with water (50 mL)
  4. extractionextracted with ether (3×50 mL)
  5. washThe organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto obtain a black froth
  9. customThe froth was chromatographed on silica gel (twice: eluant 4% MeOH/CH3Cl2 and eluant 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e059adb066934a38861ed3c92415ab21
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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