1-Chloro-4-nitrobenzene → HCID 12692632, compound

HRID 1792745Notes

Reaction equation

HRID 1792745 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1.Cl[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 127654-MethoxybenzenethiolHCID 24758Sodium hydride

Product 1

HCID 12692632HCID 12692632, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

To a suspension of NaH (4.2 g) in 100 mL of dry DMF under nitrogen was slowly added 14.02 g of 4-methoxythiophenol. The reaction mix was stirred until no further gas evolution occurred (circa 20 minutes). To this solution was added 15.76 g of 4-chloronitrobenzene dissolved in 100 ml of dry DMF, after which the mixture was heated to 120° C. for one hour. The reaction mix became red in colour during this time. The mixture was then cooled to room temperature and poured over 1000 g of crushed ice. The resulting yellow solid was filtered, washed several times with water, and dried to afford 25.29 g (96%) of 4-(4-methoxy-phenylsulfanyl)-nitrobenzene as a yellow solid. MS M+H; 264.

Workup

  1. additionThe reaction mix
  2. custom(circa 20 minutes)
  3. additionThe reaction mix
  4. temperatureThe mixture was then cooled to room temperature
  5. filtrationThe resulting yellow solid was filtered
  6. washwashed several times with water
  7. customdried

Sources & evidence

ORD record
ord-e8d135ce721f44c28b38da57cc1c2746
Source dataset
uspto-grants-2006_07
Patent number
US07078401B2

Reaction notes

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