Water → HCID 23355188, compound

HRID 234662Notes

Reaction equation

HRID 234662 reaction equation
Cl.[NH2:2][C:3]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])=O.[CH3:19][S:20][C:21](SC)=[CH:22][N+:23]([O-:25])=[O:24].O>C(O)(=O)C>[Cl:18][C:15]1[CH:14]=[C:4]2[C:3](=[CH:17][CH:16]=1)[N:2]=[C:21]([S:20][CH3:19])[C:22]([N+:23]([O-:25])=[O:24])=[C:5]2[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13]

Participants

5

Reactant 3

HCID 962WaterHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 23355179HCID 23355179, compound

Product 1

HCID 23355188HCID 23355188, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-amino-2',5-dichlorobenzophenone hydrochloride (1.6 g, 5.3 mmol) and 1,1-bis(methylthio)-2-nitroethylene (875 mg, 5.3 mmol) in 12 ml acetic acid was heated at 120° C. overnight. The reaction mixture was cooled to room temperature, 30 ml of water was added and the resulting mixture was extracted with 2×60 ml ethyl acetate. The ethyl acetate extracts were washed with 2×50 ml water, 2×50 ml saturated sodium bicarbonate solution and 50 ml brine, and then dried (anhydrous sodium sulfate), filtered and concentrated in vacuo. The residue was chromatographed on silica gel (440 g, 230-400 mesh), eluting with 85:15 hexane/ethyl acetate to yield the title compound as a yellow solid (1.65 g, 72% yield).

Workup

  1. extractionthe resulting mixture was extracted with 2×60 ml ethyl acetate
  2. washThe ethyl acetate extracts were washed with 2×50 ml water, 2×50 ml saturated sodium bicarbonate solution and 50 ml brine
  3. dry with materialdried (anhydrous sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel (440 g, 230-400 mesh)
  7. washeluting with 85:15 hexane/ethyl acetate

Sources & evidence

ORD record
ord-4b868d0f107941afbf95a6a25500e8cb
Source dataset
uspto-grants-1997_01
Patent number
US05596001

Reaction notes

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