Sodium sulfide nonahydrate → HCID 22629952, compound

HRID 2306875Notes

Reaction equation

HRID 2306875 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].O.O.O.O.O.O.O.O.O.[S-2:21].[Na+].[Na+].[Cl:24][C:25]1[C:33]([CH2:34]Cl)=[CH:32][C:28]2[O:29][CH2:30][O:31][C:27]=2[CH:26]=1>CN(C=O)C.O.C(OCC)(=O)C>[Cl:24][C:25]1[C:33]([CH2:34][S:21][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])=[CH:32][C:28]2[O:29][CH2:30][O:31][C:27]=2[CH:26]=1

Participants

7

Reactant 3

HCID 73972Sodium sulfide nonahydrateHCID 792244-Bromo-3-nitrotolueneHCID 901136-Chloropiperonyl chloride

Product 1

HCID 22629952HCID 22629952, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

1-bromo-4-methyl-2-nitrobenzene (3 mmol) dissolved in DMF (3 mL) was combined with a solution of sodium sulfide nonahydrate (3 mmol) in water 3 (mL) and stirred for 48 hours. A solution of 5-chloro-6-(chloromethyl)-1,3-benzodioxole (3 mmol) in ethyl acetate (5 mL) was added in and the reaction was agitated for another 24 hours. The reaction was diluted with ethyl acetate and washed sequentially with 0.5 N NaOH solution (7 mL×1), water (7 mL×3) and brine (7 mL×1). The solvent was removed under a stream of nitrogen and the residue crystallized from a mix of dichloromethane and hexane.

Workup

  1. stirringwas agitated for another 24 hours
  2. washwashed sequentially with 0.5 N NaOH solution (7 mL×1), water (7 mL×3) and brine (7 mL×1)
  3. customThe solvent was removed under a stream of nitrogen
  4. customthe residue crystallized from
  5. additiona mix of dichloromethane and hexane

Sources & evidence

ORD record
ord-d722416536a3436da8bfa078e54c860b
Source dataset
uspto-grants-2004_12
Patent number
US06828446B2

Reaction notes

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