Ethanolamine → Hydroxy ethylmaleimide

HRID 23965ノート

反応式

HRID 23965 の反応式
[CH2:1]([CH2:3][NH2:4])O.C1[CH:10]2[O:11]C([CH:8]3[C:15](=O)[O:14]C(=O)[CH:9]32)C=1.C([OH:19])C>>[OH:14][CH2:15][CH2:8][C:9]1[C:10]([NH:4][C:3](=[O:19])[CH:1]=1)=[O:11]

参加物

4

反応物 3

HCID 700EthanolamineHCID 702EthanolHCID 984843a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione

生成物 1

HCID 22337974Hydroxy ethylmaleimide

反応条件

温度
0 °C

実験手順

Ethanolamine (80.96 g, 1.32 mol) was added to 500 mL of ethanol and cooled to 0° C. using an ice bath. 3,6-Endoxo-1,2,3,6-tetrahydrophthalic anhydride (220.21 g, 1.32 mol) was added to the solution and allowed to stir overnight. The yellow tinted crystals were used without purification. The solution was refluxed for four hours with azeotropic removal of water. The solution was cooled to 0° C. and the resulting crystals filtered (151.74 g, 54.95%). Removal of furan was facilitated by refluxing the crystals in xylenes for 4 hours with quantitative yield of hydroxy ethylmaleimide after purification by sublimation to yield white crystals, —CH2O—), 134.2 (2C, —CH═CH—), 171.2 (2C, —NC═O m.p. 68° C. 1H-NMR (CDCl3, δ, ppm): 2.62 (1H, —OH, s), 3.82-3.77 (4H, —NCH2CH2O—, overlapping), 6.76 (2H, —CH═CH—, s). 13C-NMR (CDCl3, δ, ppm): 40.5 (1C, —NCH2—), 60.5 (1C,).

後処理

  1. customThe yellow tinted crystals were used without purification
  2. temperatureThe solution was refluxed for four hours with azeotropic removal of water
  3. temperatureThe solution was cooled to 0° C.
  4. filtrationthe resulting crystals filtered (151.74 g, 54.95%)
  5. customRemoval of furan

出典と根拠

ORDレコード
ord-3710d84d2a0043e5b0414d16ae327ec5
出典データセット
uspto-grants-2005_02
特許番号
US06855745B2

反応ノート

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