Sodium Bicarbonate → 3-bromo-4-chloro-N-(2-hydroxy-6-methyl-phenyl)-benzamide

HRID 448862Notes

Reaction equation

HRID 448862 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].C([O-])(O)=O.[Na+].[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:19](Cl)=[O:20]>C(#N)C.O>[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:19]([NH:1][C:2]1[C:3]([CH3:9])=[CH:4][CH:5]=[CH:6][C:7]=1[OH:8])=[O:20]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 30141382-Amino-m-cresolHCID 202297303-Bromo-4-chlorobenzoyl chloride

Product 1

HCID 686028573-bromo-4-chloro-N-(2-hydroxy-6-methyl-phenyl)-benzamideYield 82.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2-Amino-m-cresol (4.9 g, 40 mmol) was dissolved in a mixture of acetonitrile (90 mL) and water (80 mL) containing NaHCO3 (6.7 g, 80 mmol) with vigorous stirring. 3-Bromo-4-chloro-benzoyl chloride (10.1 g, 40 mmol, Step 2A) was added in several portions and the mixture was stirred at room temperature for 3 hrs. The resulting precipitates were filtered, washed with water and tert-butyl methyl ether, then dried to yield 3-bromo-4-chloro-N-(2-hydroxy-6-methyl-phenyl)-benzamide (11.3 g). MS (M+H)+: 339.7/341.7; tR=2.36 min. (method 1)

Workup

  1. customThe resulting precipitates
  2. filtrationwere filtered
  3. washwashed with water and tert-butyl methyl ether
  4. customdried

Sources & evidence

ORD record
ord-0ad007cdd2cd49b2a8cc11acb4e8ced5
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

Loading…