Pyridine → HCID 19861647, compound

HRID 1165417Notes

Reaction equation

HRID 1165417 reaction equation
[S:1](Cl)(Cl)=[O:2].O[N:6]=[C:7]([NH2:20])[CH2:8][C:9]1[C:18]([Br:19])=[CH: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>[Br:19][C:18]1[C:9]([CH2:8][C:7]2[NH:20][S:1][O:2][N:6]=2)=[CH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 54061589HCID 54061589, compound

Product 1

HCID 19861647HCID 19861647, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (2.0M/CH2Cl2 ; 7.4 mL, 0.015 mol) was added dropwise to a stirred suspension of N'-hydroxy-(3-bromo-2-naphthalenyl)ethanimidamide (3.29 g, 0.012 mol), methylene chloride (125 mL) and pyridine (2.4 mL, 0.03 mol) at 5° C. After 20 minutes at -5° C., the reaction solution was added to ice/H2O. The organic layer was separated, washed with saturated NaCl, dried over MgSO4 and concentrated in vacuo to a slurry (20 mL). Diethyl ether (20 mL) was added and the title compound (1.40 g, yield 36%) was collected (153°-154° C. decomp.).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated NaCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo to a slurry (20 mL)
  5. additionDiethyl ether (20 mL) was added

Sources & evidence

ORD record
ord-eb68e82da1e34d17968aeeed20fa6955
Source dataset
uspto-grants-1990_03
Patent number
US04910019

Reaction notes

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