Diethyl Ether → 3-Ethyl-5-hexylsulfonamido-2-methylbenzoxazolium p-toluenesulfonate

HRID 344993

反応式

HRID 344993 の反応式
[CH2:1]([S:7]([NH:10][C:11]1[CH:12]=[CH:13][C:14]2[O:18][C:17]([CH3:19])=[N:16][C:15]=2[CH:20]=1)(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:21]1([CH3:33])[CH:26]=[CH:25][C:24]([S:27]([O:30]CC)(=[O:29])=[O:28])=[CH:23][CH:22]=1.[CH2:34](OCC)[CH3:35]>CO>[C:21]1([CH3:33])[CH:22]=[CH:23][C:24]([S:27]([O-:30])(=[O:28])=[O:29])=[CH:25][CH:26]=1.[CH2:34]([N+:16]1[C:15]2[CH:20]=[C:11]([NH:10][S:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])(=[O:9])=[O:8])[CH:12]=[CH:13][C:14]=2[O:18][C:17]=1[CH3:19])[CH3:35]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 6638Ethyl p-methylbenzenesulfonateHCID 150510645-Hexylsulfonamido-2-methylbenzoxazole

生成物 1

HCID 199934523-Ethyl-5-hexylsulfonamido-2-methylbenzoxazolium p-toluenesulfonate収率 23%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
150 °C

実験手順

A mixture of 60 grams (0.2 Mol) 5-hexylsulfonamido-2-methylbenzoxazole and 44 grams (0.22 Mol) ethyl p-toluenesulfonate was heated in a round bottom flask at 150° C. for 5 minutes. Upon cooling to room temperature the crude brown mass almost solidified. The product was dissolved in 25 mL methanol and poured into 300 mL diethyl ether with rapid stirring for one hour. The solid precipitate was chilled at 2° C. for 12 hours, then filtered. The tan powder was thoroughly washed with ether and recrystallized from 200 mL hot isopropyl alcohol to yield 23.4 grams (47 mMol, 23% yield) of white crystalline product, m.p.=159°-161° C.

後処理

  1. temperatureUpon cooling to room temperature the crude brown mass
  2. temperatureThe solid precipitate was chilled at 2° C. for 12 hours
  3. filtrationfiltered
  4. washThe tan powder was thoroughly washed with ether
  5. customrecrystallized from 200 mL hot isopropyl alcohol

出典と根拠

ORDレコード
ord-3643c870cb7b4b4b897b06fdf136c84a
出典データセット
uspto-grants-1991_10
特許番号
US05055387

関連ノート

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