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4-Nitrophenol → 3-Ethyl-5-acrylamido-2-methylbenzoxazolium p-toluene sulfonate

HRID 5507
노트
인쇄 미리보기

반응식

HRID 5507 반응식
[C:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([CH3:14])=[N:11][C:10]=2[CH:15]=1)(=[O:4])[CH:2]=[CH2:3].[C:16]1([CH3:28])[CH:21]=[CH:20][C:19]([S:22]([O:25]CC)(=[O:24])=[O:23])=[CH:18][CH:17]=1.[CH3:29][C:30](N(C)C)=O.C1C([N+]([O-])=O)=CC=C(O)C=1>C(OCC)C>[C:16]1([CH3:28])[CH:17]=[CH:18][C:19]([S:22]([O-:25])(=[O:23])=[O:24])=[CH:20][CH:21]=1.[CH2:29]([N+:11]1[C:10]2[CH:15]=[C:6]([NH:5][C:1](=[O:4])[CH:2]=[CH2:3])[CH:7]=[CH:8][C:9]=2[O:13][C:12]=1[CH3:14])[CH3:30]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 9804-NitrophenolHCID 6638Ethyl p-methylbenzenesulfonateHCID 31374DimethylacetamideHCID 19796105N-(2-Methylbenzo[d]oxazol-5-yl)acrylamide

생성물 1

HCID 197961023-Ethyl-5-acrylamido-2-methylbenzoxazolium p-toluene sulfonate

시약·촉매·용매 1

HCID 3283
Diethyl Ether
용매

반응 조건

온도
120 °C

실험 절차

About 100 parts of (3) are combined with about 109 parts of ethyl p-toluene sulfonate, 100 ml dimethylacetamide, and 5 ml p-nitrophenol (to inhibit polymerization) in a 500 ml three-necked flask equipped with a mechanical stirrer and condenser. The reaction mixture is heated at about 120° C. for about 5 hours while stirring under argon, then stirred at room temperature for about 15 hours, monitored using thin layer chromatography (TLC). After the reaction mixture is cooled to room temperature, it is poured into about 1500 ml of dry ethyl ether, decanted and stirred in fresh ethyl ether. The ethyl ether procedure is repeated until the oil product changes to a tacky solid which is then allowed to stand in ethyl ether overnight. The solid is filtered off and washed several times with butyronitrile to remove all starting material. The solid is washed further with ethyl ether and dried to yield 3-ethyl-5-acrylamido-2-methylbenzoxazolium p-toluene sulfonate (4) as a mustard-yellow solid.

후처리

  1. customequipped with a mechanical stirrer and condenser
  2. stirringstirred at room temperature for about 15 hours
  3. temperatureAfter the reaction mixture is cooled to room temperature
  4. customdecanted
  5. stirringstirred in fresh ethyl ether
  6. filtrationThe solid is filtered off
  7. washwashed several times with butyronitrile
  8. customto remove all starting material
  9. washThe solid is washed further with ethyl ether
  10. customdried

출처 및 근거

ORD 기록
ord-b701611ad3e041048caec74b4e9736d0
출처 데이터셋
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05244994

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