(5-Nitro-2-sulfanylphenyl)methanol → HCID 19045546, compound

HRID 1591176Notes

Reaction equation

HRID 1591176 reaction equation
[SH:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][OH:5].N1C=CC=CC=1[CH2:19][CH2:20][CH:21]1[CH2:26][C:25](=O)[CH2:24][CH2:23][NH:22]1>C(Cl)(Cl)Cl>[N+:10]([C:7]1[CH:8]=[CH:9][C:2]2[S:1][C:25]3([CH2:24][CH2:23][N:22]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[CH2:21][CH2:26]3)[O:5][CH2:4][C:3]=2[CH:6]=1)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 54329580(5-Nitro-2-sulfanylphenyl)methanolHCID 86746766HCID 86746766, compound

Product 1

HCID 19045546HCID 19045546, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

2-Mercapto-5-nitrobenzyl alcohol (150 mg, 0.81 mmol) and 208 mg (0.80 mm) of N-[2-(2'-pyridylethyl]-4-piperidone was dissolved in 5 mL of CHCl3. HCl Gas was bubbled in to saturate the solution, the mixture stirred at 25° C. for 2 days, then diluted with water and the pH adjusted to 10.0 with 40% aqueous NaOH. Extraction with CHCl3 and drying the organic phase (Na2SO4) gave after concentration and recrystallization from ethyl acetate 75 mg of an orange solid.

Workup

  1. customHCl Gas was bubbled in
  2. concentrationto saturate the solution
  3. additiondiluted with water
  4. extractionExtraction with CHCl3
  5. dry with materialdrying the organic phase (Na2SO4)
  6. customgave
  7. concentrationafter concentration and recrystallization from ethyl acetate 75 mg of an orange solid

Sources & evidence

ORD record
ord-1a2810c8769c4e04add6d2d2b90ec0db
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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