Aniline → HCID 21544538、化合物

HRID 1606780ノート

反応式

HRID 1606780 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(O[CH2:19][CH:20]1[CH2:24][CH2:23][CH:22]([CH2:25]OS(C2C=CC(C)=CC=2)(=O)=O)[O:21]1)(C1C=CC(C)=CC=1)(=O)=O.COCCOCCOCCOC>[OH-].[Na+]>[C:2]1([N:1]2[CH2:25][CH:22]3[O:21][CH:20]([CH2:24][CH2:23]3)[CH2:19]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6115AnilineHCID 8189TriglymeHCID 259634(Tetrahydrofuran-2,5-diyl)bis(methylene) bis(4-methylbenzenesulfonate)

生成物 1

HCID 21544538HCID 21544538、化合物

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

反応条件

温度
185 °C

実験手順

Aniline (1.2 mole, 111.8 grams) was added to a mixture of 2,5-bis(tosyloxymethyl)tetrahydrofuran, represented by formula (II), (0.4 mole, 176.2 grams) and 300 ml of Ansul 161 (triethylene glycol dimethyl ether) and the reaction mixture heated for 4 hours at 185° C. The reaction mixture was cooled to room temperature and neutralized with a methanolic sodium hydroxide solution (32 grams NaOH in 300 ml CH3OH). Sodium tosylate was filtered and Ansul 161 and excess aniline stripped from the filtrate under aspirator pressure. 3-Phenyl-8-oxa-3-azabicyclo(3.2.1)octane, represented by formula (XX), was distilled at 113° C./0.15 mm Hg. The product solidified on standing and after recrystallization from methanol had a melting point of 84°-85° C.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationSodium tosylate was filtered
  3. distillationwas distilled at 113° C./0.15 mm Hg
  4. customafter recrystallization from methanol

出典と根拠

ORDレコード
ord-e5e6d216ed714becad07c8e5f199051e
出典データセット
uspto-grants-1976_04
特許番号
US03953596

反応ノート

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