Hydrochloric Acid → HCID 53642910, compound

HRID 1418549Notes

Reaction equation

HRID 1418549 reaction equation
S(Cl)(Cl)(=O)=O.[CH2:6]([S:8][CH:9]([CH2:14][CH3:15])[CH2:10][N+:11]([O-:13])=[O:12])[CH3:7].C(N(CC)CC)C.Cl>C(Cl)Cl>[CH2:6]([S:8][C:9]([CH2:14][CH3:15])=[CH:10][N+:11]([O-:13])=[O:12])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 53653806HCID 53653806, compound

Product 1

HCID 53642910HCID 53642910, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-Ethylthio-1-nitrobutene was prepared by adding a solution of sulfuryl chloride (20.16 g., 0.149 mol) in methylene chloride (30 ml.) to a stirred solution of 2-ethylthio-1-nitrobutane (23.02 g., 0.141 mol) in methylene chloride (100 ml.) at 0° C. The resulting solution was stirred for 15 minutes after addition was complete, and the volatile components were removed under reduced pressure. The residue was dissolved in methylene chloride (100 ml.) and a solution of triethylamine (14.27 g., 0.141 mol) in methylene chloride (30 ml.) was added at 0C. Once addition was complete, the solution was stirred for 15 minutes, and then was poured into dilute aqueous hydrochloric acid solution (400 ml.). The organics were separated and washed with deionized water (2×75 ml.), dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography(10:1 hexanes/ethyl acetate) yielded the product as a yellow oil, 2.85 g., 13% yield. 1H-NMR (CDCl3): δ 1.26, m, 3H, --CH3 ; 1.36, m, 3H, --CH3 ; 2.55, q, 2H, --CH2 --; 2.92, q, 2H, SCH2 --; 7.2, s, 1H, olefinic H.

Workup

  1. additionafter addition
  2. customthe volatile components were removed under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride (100 ml.)
  4. additionOnce addition
  5. stirringthe solution was stirred for 15 minutes
  6. customThe organics were separated
  7. washwashed with deionized water (2×75 ml.)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by silica gel chromatography(10

Sources & evidence

ORD record
ord-f6c4f1e3f6974477947e71e4d64f5c0c
Source dataset
uspto-grants-1999_03
Patent number
US05883134

Reaction notes

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