5-Bromo-6-nitroindane → HCID 20296560, compound

HRID 1389519Notes

Reaction equation

HRID 1389519 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:7][CH2:6][CH2:5]2.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[SH:20]>CN(C)C=O>[N+:11]([C:10]1[CH:9]=[C:8]2[C:4](=[CH:3][C:2]=1[S:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=1)[CH2:5][CH2:6][CH2:7]2)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 128870515-Bromo-6-nitroindaneHCID 178418616HCID 178418616, compound

Product 1

HCID 20296560HCID 20296560, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.8 g. of 5-bromo-6-nitroindan, 4.5 g. of potassium tert.-butylate, 4.4 g. of 2-pyridinethiol are heated in 50 ml. of absolute dimethylformamide for 3 hours under nitrogen to 80°. The mixture is concentrated under vacuum; the residue is combined with ethyl acetate and extracted four times with water. The ethyl acetate phase is concentrated, and the residue is purified on a silica gel column (system: cyclohexane/ethyl acetate 4:1). After crystallization from ethanol, 3.3 g. of 5-nitro-6-(2-pyridylthio)indan is obtained, m.p. 74°.

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. extractionextracted four times with water
  3. concentrationThe ethyl acetate phase is concentrated
  4. customthe residue is purified on a silica gel column (system: cyclohexane/ethyl acetate 4:1)
  5. customAfter crystallization from ethanol, 3.3 g

Sources & evidence

ORD record
ord-b795cdbcda944930b1fad1f3e319dbef
Source dataset
uspto-grants-1981_01
Patent number
US04244960

Reaction notes

Loading…