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

HRID 344993

반응식

HRID 344993 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-toluenesulfonate수율 23%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
150 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3643c870cb7b4b4b897b06fdf136c84a
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05055387

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