Acetic Anhydride → HCID 53775559, compound

HRID 1034166Notes

Reaction equation

HRID 1034166 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=NCCCC.C(OC(=O)C)(=O)C.[N+:26]([CH2:29][C:30](=[O:32])[CH3:31])([O-:28])=[O:27]>C1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=[C:29]([N+:26]([O-:28])=[O:27])[C:30](=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 662962-Propanone, 1-nitro-HCID 19023626HCID 19023626, compound

Product 1

HCID 53775559HCID 53775559, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a 2 liter 4-neck round-bottom flask fitted with mechanical stirrer and thermowell, under a nitrogen atmosphere, was added 138.2 g of N-{2-[(4-chlorobutyl)thio]phenylmethylene}-1-butanamine and 350 ml of benzene, followed by 91.9 ml of acetic anhydride. The mixture was cooled in an ice water bath as 50.18 g of nitroacetone was added. The bath was permitted to warm to room temperature and the reaction stirred overnight. The solvent was removed by rotary evaporation and the product was partitioned between ether and sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated to dryness. Purification via column chromatograph on silica gel, eluting with 15% ethyl acetate in hexane provided the product as a pale orange oil. Mass spectrum: 314 (M+1).

Workup

  1. customTo a 2 liter 4-neck round-bottom flask fitted with mechanical stirrer
  2. additionwas added
  3. customThe solvent was removed by rotary evaporation
  4. customthe product was partitioned between ether and sodium bicarbonate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness
  8. customPurification via column chromatograph on silica gel
  9. washeluting with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a189253b71814e23be784887af89b937
Source dataset
uspto-grants-1994_05
Patent number
US05314887

Reaction notes

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