Water → HCID 2799727, compound

HRID 2224052Notes

Reaction equation

HRID 2224052 reaction equation
[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13]([O:20][CH3:21])[CH:12]=1.O>CN(C)C=O>[CH3:21][O:20][C:13]1[CH:12]=[C:11]([S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:16]=[CH:15][C:14]=1[N+:17]([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 811105-Chloro-2-nitroanisole

Product 1

HCID 2799727HCID 2799727, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Using the procedure reported in Chem. Pharm. Bull. 40(2), 351-6, 1992, sodium hydride (60% suspension in mineral oil, 1.26 g, 44 mmol) was added to 40 mL of dimethyl formamide (DMF) at 0° C., and a solution of benzenethiol (2.25 g, 22 mmol) in 5 mL of DMF was added dropwise over five minutes, followed by stirring for 30 minutes. A solution of 4-chloro-2-methoxy-1-nitro-benzene (3.25 g, 20 mmol) in 25 mL of DMF was then added dropwise to the reaction mixture over 30 minutes, after which stirring was continued for another hour. Sixty mL of water was added to the reaction mixture, and a solid precipitated and was collected and dried under vacuum to yield 4.63 g (17.7 mmol, 89%) of 2-methoxy-1-nitro-4-phenylsulfanyl-benzene. MS: 262 (M+H)+.

Workup

  1. stirringafter which stirring
  2. waitwas continued for another hour
  3. customa solid precipitated
  4. customwas collected
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7339336d7411463c8c7f58a613d6dadf
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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