Benzoyl chloride → HCID 67891722, compound

HRID 2405456Notes

Reaction equation

HRID 2405456 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)[CH:5]=[CH:6][CH:7]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+].[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 68897890HCID 68897890, compound

Product 1

HCID 67891722HCID 67891722, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

3.8 g (13 mmol) of (3-bromophenyl)-(2-nitrophenyl)amine was dissolved in 30 mL of tetrahydrofuran. A solution of 11 g (64 mmol) of sodium hydrosulfite in 30 mL of water was added dropwise to the solution while stirring the solution at room temperature in an argon atmosphere. After stirring the mixture for 5 hours, 20 mL of ethyl acetate was added to the mixture. A solution of 2.2 g (26 mmol) of sodium hydrogencarbonate in 20 mL of water was then added to the mixture. After the dropwise addition of a solution of 2.5 g (18 mmol) of benzoyl chloride in 10 mL of ethyl acetate, the mixture was stirred at room temperature for 1 hour. The mixture was then extracted with ethyl acetate, washed with a 10% potassium carbonate aqueous solution, water, and a saturated sodium chloride solution sequentially, and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure to obtain N-[2-(3-bromophenylamino)phenyl]benzamide.

Workup

  1. stirringAfter stirring the mixture for 5 hours
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washwashed with a 10% potassium carbonate aqueous solution, water
  5. dry with materiala saturated sodium chloride solution sequentially, and dried over anhydrous sodium sulfate
  6. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-19c578ba6a3a45afb03002c821bb469a
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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