Pyridine → phenyl 1-(4-chlorophenyl)-3-methyl-1H-pyrazol-5-yl-carbamate

HRID 1864659ノート

反応式

HRID 1864659 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([NH2:13])=[CH:11][C:10]([CH3:14])=[N:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([NH:13][C:22](=[O:23])[O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:11][C:10]([CH3:14])=[N:9]2)=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 1703011H-Pyrazol-5-amine, 1-(4-chlorophenyl)-3-methyl-

生成物 1

HCID 46196893phenyl 1-(4-chlorophenyl)-3-methyl-1H-pyrazol-5-yl-carbamate収率 26.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

1-(4-chlorophenyl)-3-methyl-1H-pyrazol-5-amine (100 mg, 0.48 mmol) was dissolved in dry THF (6 mL). Pyridine (51 μL, 0.62 mmol) was added and the solution was cooled in an ice bath under nitrogen surpressure. Phenyl chloroformate (73 μL, 0.58 mmol) was slowly added and the mixture was stirred at 0° C. during 5 min and at room temperature during 1.5 h. The mixture was then diluted in EtOAc (10 mL) and the salts remaining were filtrated off. The filtrate was concentrated under reduced pressure. The resulting white solid was washed with a little amount of cold EtOAc and water to afford the title compound (41 mg, 26%) as a white solid. 1H-NMR (δ, ppm, DMSO-d6): 2.22 (s, 3H, CH3), 6.28 (s, 1H, HPyz,4), 7.11-7.60 (m, 9H, Harom), 10.14 (bs, 1H, NH). LC-MS (m/z): 328 (M+H, 100).

後処理

  1. temperaturethe solution was cooled in an ice bath under nitrogen surpressure
  2. filtrationthe salts remaining were filtrated off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washThe resulting white solid was washed with a little amount of cold EtOAc and water

出典と根拠

ORDレコード
ord-faeac165ae834c989671081f98697087
出典データセット
uspto-grants-2009_12
特許番号
US07625922B2

反応ノート

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