Water → N'-(4-benzyloxy-2-methylphenyl)-N-(4-fluorophenyl)-N'-methylurea

HRID 853542

反応式

HRID 853542 の反応式
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][C:4]=1[CH3:17].[H-].[Na+].[F:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:36])OC2C=CC=CC=2)=[CH:23][CH:22]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:10]([O:9][C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:1])[C:28](=[O:36])[NH:27][C:24]2[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=2)=[C:4]([CH3:17])[CH:5]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10751974Phenyl N-(4-fluorophenyl)carbamateHCID 22936498N-Methyl-4-benzyloxy-2-methylaniline

生成物 1

HCID 22936785N'-(4-benzyloxy-2-methylphenyl)-N-(4-fluorophenyl)-N'-methylurea収率 62.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

After dissolving N-methyl-4-benzyloxy-2-methylaniline (2.64 g, 11.61 mmol) in N,N-dimethylformamide (20 ml), sodium hydride (1.16 g, 29.00 mmol, 60% in oil) was added and the mixture was stirred at 85° C. for 45 minutes under a nitrogen atmosphere. Phenyl N-(4-fluorophenyl)carbamate (3.50 g, 12.76 mmol) was added and the mixture was further stirred at 85° C. for 1 hour under a nitrogen atmosphere. After cooling to room temperature, water was added to the reaction solution, extraction was performed with ethyl acetate, the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was adsorbed onto NH silica gel and subjected to crude purification by NH silica gel column chromatography (hexane-ethyl acetate-ethanol) to obtain N′-(4-benzyloxy-2-methylphenyl)-N-(4-fluorophenyl)-N′-methylurea (2.66 g) as a yellow oil. This was dissolved in methanol (50 ml), and then 10% palladium carbon (0.2 g) was added and the mixture was stirred for 2 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and then filtrate was washed with ethanol, and the solvent was distilled off under reduced pressure. The precipitated crystals were suspended in ethanol, the suspension was diluted with diethyl ether and hexane, and the crystals were filtered out, washed with hexane and dried by aspiration to obtain the title compound (0.83 g, 3.0258 mmol, 41.86%) as brown crystals.

後処理

  1. additionwas added
  2. stirringthe mixture was further stirred at 85° C. for 1 hour under a nitrogen atmosphere
  3. temperatureAfter cooling to room temperature
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. custompurification by NH silica gel column chromatography (hexane-ethyl acetate-ethanol)

出典と根拠

ORDレコード
ord-7ba000cfe3ed41b08c16bfcc91fc8fd3
出典データセット
uspto-grants-2007_08
特許番号
US07253286B2

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