2-Nitrobenzenesulfenyl chloride → HCID 15136149, compound

HRID 1651045Notes

Reaction equation

HRID 1651045 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[CH:13]=[CH:14][CH:15]=[C:16]([S:17]C(=O)N(C)C)[C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2].[N+:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32]Cl)([O-:25])=[O:24]>ClCCCl.[Cl-].[Zn+2].[Cl-]>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[CH:13]=[CH:14][CH:15]=[C:16]([S:17][S:32][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[N+:23]([O-:25])=[O:24])[C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 243192-Nitrobenzenesulfenyl chlorideHCID 14306461HCID 14306461, compound

Product 1

HCID 15136149HCID 15136149, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 0.32 g (1 mmol) of 3-ethoxycarbonyl-9-(dimethylcarbamoylthio)-4-oxo-4H-pyrido[1,2-a]pyrimidine (I d'-1) in 10 ml of dry 1,2-dichloroethane are added 0.2 g (1.5 mmol) of 2-nitrophenylsulphenyl chloride (X) and 0.2 g (1.5 mmol) of zinc chloride, and the resultant mixture is stirred for 35 minutes at room temperature. After the mixture is diluted with 1,2-dichloroethane, it is washed with N-HCl, 5% NaHCO3 and saturated brine in order. The organic layer is dried over sodium sulfate and concentrated under reduced pressure. The residue in 0.5 g is recrystallized from ethyl acetate-methylene chloride to give 0.365 g (Yield: 90.9%) of the titled compound (I e-1).

Workup

  1. washis washed with N-HCl, 5% NaHCO3 and saturated brine in order
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue in 0.5 g is recrystallized from ethyl acetate-methylene chloride

Sources & evidence

ORD record
ord-b0de64e7f3c2417dbfc58a81963f489d
Source dataset
uspto-grants-1990_05
Patent number
US04927829

Reaction notes

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