2-(Trimethylstannyl)-1,3-thiazole → 4-(Tetradecyloxy)-N-[3-(2-thiazolyl)phenyl]benzeneacetamide

HRID 483591ノート

反応式

HRID 483591 の反応式
I[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:32])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.C[Sn](C)(C)[C:35]1[S:36][CH:37]=[CH:38][N:39]=1>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:35]3[S:36][CH:37]=[CH:38][N:39]=3)[CH:3]=2)=[O:32])=[CH:12][CH:13]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

参加物

5

反応物 2

HCID 129566412-(Trimethylstannyl)-1,3-thiazoleHCID 15030163N-(3-Iodophenyl)-4-(tetradecyloxy)benzeneacetamide

生成物 1

HCID 150301644-(Tetradecyloxy)-N-[3-(2-thiazolyl)phenyl]benzeneacetamide収率 19.5%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 10 g of N-[3-iodophenyl)-4-(tetradecyloxy)benzeneacetamide, 4.96 g of 2-(trimethylstannyl)thiazole, and 638.62 mg of dichlorobis(triphenylphosphine)palladium (II) in 100 ml of tetrahydrofuran is refluxed under argon for 6 hours. The solvent is evaporated and the residue is partitioned between chloroform and 1N sodium hydroxide. The organic layer is dried and evaporated to a yellow solid residue. The residue is purified by chromatography on silica gel using chloroform. A total of 3.5 g of starting material is recovered as well as impure pro duct which is crystallized from hexane:carbon tetrachloride to give 1.8 g of the desired product as a tan solid, m.p. 128°-131° C.

後処理

  1. temperatureis refluxed under argon for 6 hours
  2. customThe solvent is evaporated
  3. customthe residue is partitioned between chloroform and 1N sodium hydroxide
  4. customThe organic layer is dried
  5. customevaporated to a yellow solid residue
  6. customThe residue is purified by chromatography on silica gel
  7. customA total of 3.5 g of starting material is recovered as well as impure pro duct which
  8. customis crystallized from hexane

出典と根拠

ORDレコード
ord-8aeb8b171c7d40ef9f3dbcc26cbc8f1f
出典データセット
uspto-grants-1993_07
特許番号
US05225425

反応ノート

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