Hydrochloric Acid → N-(3-methyl-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamide

HRID 543570ノート

反応式

HRID 543570 の反応式
S(Cl)(Cl)=O.[CH3:5][C:6]1([C:9]([OH:11])=O)[CH2:8][CH2:7]1.[CH3:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][CH:21]([F:23])[F:22])[NH2:16].Cl>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH3:12][C:13]1[CH:14]=[C:15]([NH:16][C:9]([C:6]2([CH3:5])[CH2:8][CH2:7]2)=[O:11])[CH:17]=[CH:18][C:19]=1[O:20][CH:21]([F:22])[F:23]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 813261-Methylcyclopropanecarboxylic acidHCID 132950334-(Difluoromethoxy)-3-methylaniline

生成物 1

HCID 13314709N-(3-methyl-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamide収率 70.6%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 1140Toluene溶媒3 回

反応条件

温度
0 °C

実験手順

To a mixture of toluene (50 ml) and pyridine (4.2 g) cooled at 0° C., thionyl chloride (1.3 g) was added, and a solution of 1-methylcyclopropanecarboxylic acid (1.0 g) in toluene was dropwise added thereto while stirring. A solution of 3-methyl-4-difluoromethoxyaniline (1.75 g) in toluene was dropwise added thereto. After the dropwise addition was completed, stirring was continued at room temperature for 3 hours. The reaction mixture was admixed with 5% hydrochloric acid (20 ml). The organic solvent layer was separated, washed with 1% sodium hydroxide solution and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to give crude crystals (2.2 g). The crude crystals were recrystallized from ethanol to give N-(3-methyl-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamide (1.8 g). M.P., 68°-69° C.

後処理

  1. additionAfter the dropwise addition
  2. stirringstirring
  3. customThe organic solvent layer was separated
  4. washwashed with 1% sodium hydroxide solution and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto give crude crystals (2.2 g)
  8. customThe crude crystals were recrystallized from ethanol

出典と根拠

ORDレコード
ord-9df445b6a1e14df4b8755eb4f62f3a7e
出典データセット
uspto-grants-1984_05
特許番号
US04447260

反応ノート

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