Water → HCID 11067251, compound

HRID 1241691Notes

Reaction equation

HRID 1241691 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH:5]=[CH:6][CH:7]=1.O.[H-].[Na+].[CH3:22]OS(OC)(=O)=O>OS(O)(=O)=O.CN(C=O)C>[Br:1][C:2]1[C:3]2[C:11](=[O:13])[C:10]3[C:9](=[CH:17][C:16]([Cl:18])=[CH:15][CH:14]=3)[N:8]([CH3:22])[C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 13400569BENZOIC ACID, 2-[(3-BROMOPHENYL)AMINO]-4-CHLORO-2×

Product 1

HCID 11067251HCID 11067251, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

(Method E-3) 2-(3-Bromo-phenylamino)-4-chlorobenzoic acid, 14 (4 g, 12.2 mmol) was heated in conc. H2SO4 (50 ml) for 30 min then allowed to cool to room temperature. Water was added slowly and the precipitate filtered off, washed with water and dried over phosphorous pentoxide. The crude material was suspended in DMF (50 mL) and added under nitrogen to NaH (1.2 g, 50 mmol) in DMF (50 mL). After 30 min dimethylsulphate (3 ml, 18 mmol) was added and stirring continued for 1 hr. Addition of water gave a precipitate the title compound (625 mg, 2.02 mmol, 17%) as the more polar product after separation by column chromatography (ethyl acetate:hexane 1:4)

Workup

  1. filtrationthe precipitate filtered off
  2. washwashed with water
  3. dry with materialdried over phosphorous pentoxide

Sources & evidence

ORD record
ord-8cdfbf2c6ae44b11b6617ccb296ab359
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

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