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

HRID 5507

反応式

HRID 5507 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b701611ad3e041048caec74b4e9736d0
出典データセット
uspto-grants-1993_09
特許番号
US05244994

関連ノート

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