m-Toluidine → 5-Bromo-N-(3-methylphenyl)-2-[(phenylmethyl)oxy]benzamide
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[CH:33]=1>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[CH:33]=1)=[O:9]Participants
Procedure
Solid 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method B; 200 mg, 0.651 mmol) was added to a stirred suspension of CDI (106 mg, 0.651 mmol) in THF (6 ml) under nitrogen at 20° C. The reaction mixture was stirred at room temperature for 10 min and m-toluidine (69.8 mg, 0.65 mmol) was added dropwise. After refluxing for 14 h, the reaction mixture was concentrated to obtain crude product. The crude product was dissolved in 20 ml of CH2Cl2 and the organic phase was washed with 2M hydrochloric acid (5 ml), water (5×2 ml), dried over sodium sulphate and evaporated in vacuo to give yellow solid. The crude product was further purified by silica gel chromatography eluting with hexane:ethyl acetate (10:1) to yield the title compound. 120 mg.
Workup
- temperatureAfter refluxing for 14 h
- concentrationthe reaction mixture was concentrated
- customto obtain crude product
- washthe organic phase was washed with 2M hydrochloric acid (5 ml), water (5×2 ml)
- dry with materialdried over sodium sulphate
- customevaporated in vacuo
- customto give yellow solid
- customThe crude product was further purified by silica gel chromatography
- washeluting with hexane:ethyl acetate (10:1)
Sources & evidence
- ORD record
- ord-c463a4b274464fce847af5352441fb88
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778939B2
Reaction notes
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