Sodium Hydroxide → HCID 19779518, compound

HRID 2082069Notes

Reaction equation

HRID 2082069 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][CH2:13][CH2:14][CH2:15][S:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.C(=O)=O.CC(C)=O.[OH-].[Na+]>C(Cl)Cl>[Cl:12][CH2:13][CH2:14][CH2:15][S:16]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:6]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 149330551-[(3-Chloropropyl)sulfanyl]-4-nitrobenzeneHCID 18522661Acetone cardice

Product 1

HCID 19779518HCID 19779518, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperoxybenzoic acid (80% 16.6 g, 86.3 mmol) in methylene chloride (100 mL) was added dropwise to a solution of 1-[(3-chloropropyl)thio]-4-nitrobenzene (20.0 g, 86.3 mmol) in methylene chloride (20 mL) maintained at -78° C. (dry ice/acetone bath). After 2 h the reaction was allowed to warm to ambient temperature (~1 h) and 200 mL of 10% aqueous sodium hydroxide was added. The layers were allowed to separate and the aqueous layer was extracted (100 mL) with methylene chloride. The combined organic extracts were washed (water, 100 mL), dried (MgSO4) and concentrated in vacuo. A 1.0 g sample of the residue (21.2 g) was chromatographed (Chromatatron, SiO2 4000 μ, 99/1 methylene chloride:methanol) to give 0.89 g (88%) of white solid, mp 72.5°-74.5° C.

Workup

  1. additionwas added
  2. customto separate
  3. extractionthe aqueous layer was extracted (100 mL) with methylene chloride
  4. washThe combined organic extracts were washed (water, 100 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customA 1.0 g sample of the residue (21.2 g) was chromatographed (Chromatatron, SiO2 4000 μ, 99/1 methylene chloride:methanol)

Sources & evidence

ORD record
ord-91f2317980eb42fa8e946f78d07fdfc3
Source dataset
uspto-grants-1993_02
Patent number
US05187189

Reaction notes

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