3,4-Dichloroaniline → 3',4'-Dichloro-2,2-dimethylpropionanilide

HRID 1366764

反応式

HRID 1366764 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[OH-].[Na+].[C:12](Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>CC(OC)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH:6]=[CH:7][C:8]=1[Cl:9]

参加物

5

反応物 3

HCID 72573,4-DichloroanilineHCID 14798Sodium HydroxideHCID 62493Pivaloyl chloride

生成物 1

HCID 1389493',4'-Dichloro-2,2-dimethylpropionanilide

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
10 °C

実験手順

3,4-dichloroaniline (150 g) was dissolved in 1.0 L TBME and the solution was cooled to 10° C. Sodium hydroxide (140.7 g of a 30% aqueous solution) was added under mechanical stirring. Pivaloyl chloride (125.9 mL) was added dropwise while keeping the internal temperature under 35° C. After the addition, the temperature of the reaction was maintained at 30-35° C. for a further 30 min. The reaction mixture was then allowed to cool to room temperature and subsequently kept at 0-5° C. for 1 h. The resulting precipitate was filtered of and washed with 600 mL water/MeOH (90/10) and then with 900 mL water. The resulting solid was the dried in a vacuum oven at 55° C. for 4 days. Yield: 162 g. 1H-NMR (DMSO-d6) δ 9.46 (s, 1H), 8.04 (d, J=2.4 Hz, 1H), 7.65 (dd, J=9.0. 2.4 Hz, 1H), 7.54 (d, J=9.0 Hz, 1H), 1.22 (9H, s).

後処理

  1. customunder 35° C
  2. additionAfter the addition
  3. temperaturethe temperature of the reaction was maintained at 30-35° C. for a further 30 min
  4. temperatureto cool to room temperature
  5. filtrationThe resulting precipitate was filtered of and
  6. washwashed with 600 mL water/MeOH (90/10)
  7. customdried in a vacuum oven at 55° C. for 4 days

出典と根拠

ORDレコード
ord-bc5caa7b7b5344939a44d4a6182e8ff1
出典データセット
uspto-grants-2011_02
特許番号
US07893089B2

関連ノート

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