Aniline → 2-morpholin-4-ylmethyl-6-nitro-N-phenyl-benzamide
Reaction equation
[N:1]1([CH2:7][C:8]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:9]=2[C:10]([OH:12])=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[N:1]1([CH2:7][C:8]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:9]=2[C:10]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:12])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1Participants
6
Procedure
A solution of compound 6 (0.62 g, 2.3 mmol) in THF (50 mL) was treated with thionyl chloride (0.94 mL), stirred at room temperature for 4 h, and evaporated to dryness. The residue was dissolved in THF (50 mL) and treated with aniline (0.58 mL, 6.4 mmol) and diisopropylethylamine (1.12 mL, 6.4 mmol). The reaction mixture was stirred for 4 h, concentrated, dissolved in dichloromethane (50 mL), washed with saturated aqueous sodium bicarbonate (25 mL) and brine (25 mL), dried with sodium sulfate, and concentrated. The crude residue of compound 7 then was purified by flash chromatography (5% methanol in dichloromethane).
Workup
- customevaporated to dryness
- dissolutionThe residue was dissolved in THF (50 mL)
- stirringThe reaction mixture was stirred for 4 h
- concentrationconcentrated
- dissolutiondissolved in dichloromethane (50 mL)
- washwashed with saturated aqueous sodium bicarbonate (25 mL) and brine (25 mL)
- dry with materialdried with sodium sulfate
- concentrationconcentrated
- customThe crude residue of compound 7 then was purified by flash chromatography (5% methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-50adf64c1f5b4905ad6c63d130076fb1
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207153B2
Reaction notes
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