Sodium Carbonate → phenyl (3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)carbamate

HRID 63358

反応式

HRID 63358 の反応式
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26]>C(OC(C)C)(=O)C.O>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:25](=[O:26])[O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:7]([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 15891Phenyl chloroformateHCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amine2 回

生成物 1

HCID 11057211phenyl (3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)carbamate収率 89.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 7915Isopropyl Acetate溶媒

実験手順

A solution of 3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-amine (Intermediate A) (20 g, 87.0 mmol) in isopropyl acetate (240 mL) was added to a stirred solution of sodium carbonate (11.3 g, 106 mmol) in water (80 mL). After 10 min phenyl chloroformate (12.1 mL, 96 mmol) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with water (160 mL), the layers were separated and the organics were washed with water (2×80 mL), brine (80 mL), dried (MgSO4) and concentrated in vacuo. The resulting yellow solid was suspended in 10% ether/iso-hexane (320 mL) and stirred until a uniform suspension was obtained. The solid was collected by filtration and washed with iso-hexane to yield the subtitle compound phenyl (3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)carbamate as a white powder (27.3 g, 88%); Rt 2.65 min (Method 1); m/z 350 (M+H)+ (ES+); 1H NMR δ:1.29 (9H, s), 2.37 (3H, s), 6.35 (1H, s), 7.10-7.23 (3H, overlapping m), 7.33-7.46 (6H, overlapping m), 9.99 (1H, s).

後処理

  1. customthe layers were separated
  2. washthe organics were washed with water (2×80 mL), brine (80 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. stirringstirred until a uniform suspension
  6. customwas obtained
  7. filtrationThe solid was collected by filtration
  8. washwashed with iso-hexane

出典と根拠

ORDレコード
ord-001455796ea0414eb6ae0b09c4fb5f86
出典データセット
uspto-grants-2016_09
特許番号
US09447076B2

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