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

HRID 1199334

반응식

HRID 1199334 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 199934523-Ethyl-5-hexylsulfonamido-2-methylbenzoxazolium p-toluenesulfonate

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
150 °C

실험 절차

A mixture of 60 g of Intermediate A and 44 g 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 was almost solidified. The product was dissolved in 25 ml methanol and poured into 300 ml diethyl ether with rapid stirring for 1 hour. The solid precipitate was chilled at 2° C. overnight, and then filtered. The tan powder was thoroughly washed with ether and recrystallized from 200 ml hot isopropyl alcohol to yield 23.4 g of 3-ethyl-5-hexylsulfonamido-2-methylbenzoxazolium p-toluenesulfonate (Intermediate B).

후처리

  1. temperatureUpon cooling to room temperature
  2. temperatureThe solid precipitate was chilled at 2° C. overnight
  3. filtrationfiltered
  4. washThe tan powder was thoroughly washed with ether
  5. customrecrystallized from 200 ml hot isopropyl alcohol

출처 및 근거

ORD 기록
ord-2177c8f186f646118db4f829b6ed8660
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04900652

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