Ethylene Glycol → 2-Phenyl-ethenesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

HRID 965623ノート

反応式

HRID 965623 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5]C.C(O)CO.[Na].ClC1[N:18]=[CH:17][N:16]=[C:15]([NH:19][S:20]([CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:22])=[O:21])[C:14]=1[C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1>CN(C=O)C>[OH:5][CH2:4][CH2:3][O:2][C:1]1[N:18]=[CH:17][N:16]=[C:15]([NH:19][S:20]([CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:22])=[O:21])[C:14]=1[C:31]1[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=1

参加物

6

反応物 4

HCID 174Ethylene GlycolHCID 80711,2-DimethoxyethaneHCID 5360545Sodium2 回HCID 738818642-Phenyl-ethenesulfonic acid [6-chloro-5-p-tolyl-pyrimidin-4-yl]-amide

生成物 1

HCID 695584832-Phenyl-ethenesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 1,2-dimethoxyethan (15 ml) and ethyleneglycol (40 ml) was added sodium (298 mg) in small portions. The mixture was stirred until the sodium was completely dissolved. Then DMF (15 ml), followed by 2-phenyl-ethenesulfonic acid(6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide (1.0 g) was added. Stirring was continued for 4 days at 100° C. The mixture was evaporated and water (150 ml) was added to the residue followed by addition of acetic acid (1.0 ml). The precipitate was filtered off, washed with water and dried. The crude material was purified by chromatography over silicagel with EtOAc/methanol/aqueous ammonia (25%)=4/1/0.5 to give 2-phenyl-ethenesulfonic acid[6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (500 mg). tR=4.54 (LC); M+=412.38 (ES+).

後処理

  1. dissolutionwas completely dissolved
  2. additionwas added
  3. customThe mixture was evaporated
  4. additionwater (150 ml) was added to the residue
  5. additionfollowed by addition of acetic acid (1.0 ml)
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customdried
  9. customThe crude material was purified by chromatography over silicagel with EtOAc/methanol/aqueous ammonia (25%)=4/1/0.5

出典と根拠

ORDレコード
ord-245b1ab79cd24c2aaa08c38036fadbf6
出典データセット
uspto-grants-2005_10
特許番号
US06951856B2

反応ノート

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