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

Thionyl Chloride → N-[4-[(Methylphenylamino)sulfonyl]phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 1938172
ノート
印刷プレビュー

反応式

HRID 1938172 の反応式
[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([OH:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.[C:15]1([N:21]([CH3:32])[S:22]([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C(=O)C.O>[F:1][C:2]([F:10])([F:9])[C:3]([OH:7])([CH3:8])[C:4]([NH:29][C:28]1[CH:30]=[CH:31][C:25]([S:22]([N:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH3:32])(=[O:24])=[O:23])=[CH:26][CH:27]=1)=[O:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 24386Thionyl ChlorideHCID 3085904-amino-N-methyl-N-phenylbenzenesulfonamideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid

生成物 1

HCID 9930941N-[4-[(Methylphenylamino)sulfonyl]phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide収率 60.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 31374
Dimethylacetamide
溶媒

反応条件

温度
0 °C

実験手順

To a cooled (-20° C.) solution of α-trifluoromethyl lactic acid 0.20 g in dry N,N-dimethylacetamide (4 ml) was added thionyl chloride (0.16 g). The reaction mixture was stirred for 1 hour, then warmed to 0° C. over 30 minutes and treated with 4-(N-phenyl-N-methylaminosulfonyl)aniline (0.34 g). After stirring at 22° C. for 24 hours, the reaction mixture was diluted with water (30 ml) and extracted with ethyl acetate (2×20 ml). The combined ethyl acetate extracts were washed with brine, dried (Na2SO4) and concentrated at reduced pressure to give an oil which was purified by chromatography (1:1 hexane: ethyl aceate) and recrystallised from methyl-t-butyl ether/hexane to produce the title compound as a colourless solid (0.31 g); mp 147°-149° C.; MS: m/z=403(M+1); NMR (250 MHz): 1.55 (s,3), 3.09 (s,3), 7.05-7.08 (m, 2), 7.28-7.43 (m,5), 7.53 (s,1), 7.91-7.95 (m,2), 10.36 (broad s, 1). Analysis for C17H17F3N2O4S: Calculated: C, 50.78; H, 4.26; N, 6.97; Found: C, 50.80; H, 4.37; N, 6.93.

後処理

  1. stirringAfter stirring at 22° C. for 24 hours
  2. extractionextracted with ethyl acetate (2×20 ml)
  3. washThe combined ethyl acetate extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated at reduced pressure
  6. customto give an oil which
  7. customwas purified by chromatography (1:1 hexane: ethyl aceate)
  8. customrecrystallised from methyl-t-butyl ether/hexane

出典と根拠

ORDレコード
ord-c8596caa1ea445f49483b85fff756c5e
出典データセット
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05693639

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート