ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Formaldehyde → 4-tert.-butyl-N-[6-(4-phenoxy-2-butynyloxy)-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide

HRID 2085110
ノート
印刷プレビュー

反応式

HRID 2085110 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19](Cl)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[O:29]([CH2:36][C:37]#[C:38][CH2:39][OH:40])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(OCC#C)C=CC=CC=1.C=O.[H-].[Na+]>C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19]([O:40][CH2:39][C:38]#[C:37][CH2:36][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 83613(Prop-2-ynyloxy)benzeneHCID 160466794-Phenoxybut-2-yn-1-olHCID 227294154-tert.-butyl-N-[6-chloro-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide

生成物 1

HCID 102306544-tert.-butyl-N-[6-(4-phenoxy-2-butynyloxy)-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide
収率 41.1%

試薬・触媒・溶媒 2

HCID 311Citric Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 282 mg of 4-tert.-butyl-N-[6-chloro-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide (Example 12c) and 1.10 g of 4-phenoxy-2-butyn-1-ol (prepared starting from phenyl-propargylether and para-formaldehyde following the procedure given in J. Chem. Soc. Perkin Trans. 1, 1991, 1721-1727) in 15 ml THF was added 271 mg of 55% NaH in mineral oil. The suspension was stirred for 4 h at reflux. The reaction mixture was cooled, diluted with 100 ml 10% aqueous citric acid and extracted 4 times with 50 ml of ethyl acetate. The combined organic phases were washed with water, dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel eluting with heptane:ethyl acetate 1:1 and precipitated from diethyl ether to give 151 mg of 4-tert.-butyl-N-[6-(4-phenoxy-2-butynyloxy)-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide as a white powder. LC-MS: tR=6.34 min, [M+1]+=542.48, [M−1]−=540.15.

後処理

  1. customprepared
  2. temperatureat reflux
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted 4 times with 50 ml of ethyl acetate
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe crude product was purified by column chromatography on silica gel eluting with heptane:ethyl acetate 1:1
  9. customprecipitated from diethyl ether

出典と根拠

ORDレコード
ord-f6de9c69d6a6454a9c5cd5f56bbc0ca9
出典データセット
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06720322B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート