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Phenylacetyl chloride → N-[4'-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-2-phenylacetamide

HRID 584959
ノート
印刷プレビュー

反応式

HRID 584959 の反応式
FC(F)(F)C(O)=O.[CH3:8][NH:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1.O1CCCC1.C(N(CC)CC)C.[C:43]1([CH2:49][C:50](Cl)=[O:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O>[O:29]=[C:27]1[NH:26][C:25](=[O:30])[CH:24]([CH2:23][C:20]2[CH:19]=[CH:18][C:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][N:9]([CH3:8])[C:50](=[O:51])[CH2:49][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:12]=3)=[CH:22][CH:21]=2)[S:28]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7679Phenylacetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 223414025-(3'-Methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate

生成物 1

HCID 22341517N-[4'-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-2-phenylacetamide収率 72%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

実験手順

500 mg (1.1 mmol) of 5-(3′-methylaminomethyl-biphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate, 2 ml of tetrahydrofuran and 500 μl (3.3 mmol) of triethylamine are introduced into a round-bottomed flask under a stream of nitrogen. 230 μl of phenylacetyl chloride are added dropwise and the mixture is stirred at room temperature for one hour. The reaction medium is poured into water and extracted with ethyl acetate, and the organic phase is separated out after settling of the phases has taken place, washed with water, dried over magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of dichloromethane and methanol (97/3). 360 mg(72%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-2-phenylacetamide are obtained in the form of a white solid with a melting point of 73° C.

後処理

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated out
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of dichloromethane and methanol (97/3)

出典と根拠

ORDレコード
ord-5e97a1d8c60f4c898dbf5618aeef7b9a
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06927228B2

反応ノート

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