4-Nitrophenethyl bromide → HCID 178526627, compound

HRID 1591175Notes

Reaction equation

HRID 1591175 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([S:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[S:7]2)[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31]Br)=[CH:26][CH:25]=1)([O-:23])=[O:22]>CO>[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][SH:7]2[C:4]3([CH2:3][CH2:2][NH:1][CH2:6][CH2:5]3)[S:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]2=3)=[CH:26][CH:25]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 792664-Nitrophenethyl bromideHCID 516892Sodium BicarbonateHCID 19045565HCID 19045565, compound

Product 1

HCID 178526627HCID 178526627, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 111 mgs (0.47 mmol) of dithioketal from Step A in 1 mL of methanol was added 157 mgs of sodium bicarbonate and 118 mg (0.54 mmol) of 2-(4-nitrophenyl)ethyl bromide. The reaction was refluxed for 6 hrs and then concentrated at reduced pressure. The residue was chromotographed (silica gel, 2.5% CH3OH/CH2Cl2) to give after concentration and crystallization from ethyl acetate/Hexanes, 120 mgs of product as the free base.

Workup

  1. temperatureThe reaction was refluxed for 6 hrs
  2. concentrationconcentrated at reduced pressure
  3. customto give
  4. concentrationafter concentration and crystallization from ethyl acetate/Hexanes, 120 mgs of product as the free base

Sources & evidence

ORD record
ord-b0646da8c68249c9ba4a14bee83f728e
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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