Carbon Disulfide → 1H-Pyrrole-1-carbodithioic acid phenylmethyl ester

HRID 352703ノート

反応式

HRID 352703 の反応式
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[H-].[Na+].[C:8](=[S:10])=[S:9].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CS(C)=O.C(OCC)C.O>[N:1]1([C:8]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[S:9])[CH:5]=[CH:4][CH:3]=[CH:2]1

参加物

8

反応物 4

HCID 6348Carbon DisulfideHCID 7503Benzyl ChlorideHCID 8027PyrroleHCID 24758Sodium hydride

生成物 1

HCID 121494521H-Pyrrole-1-carbodithioic acid phenylmethyl ester収率 50.1%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

Pyrrole (1.34 g, 20 mmol) was added dropwise to a stirred suspension of sodium hydride (0.48 g, 20 mmol) in dimethyl sulfoxide (20 mL). On completion of addition the resulting brown solution was stirred at room temperature for 30 minutes before the addition of carbon disulfide (1.52 g, 20 mmol). The solution was allowed to stir at room temperature for a further half hour and benzyl chloride (2.53 g, 20 mmol) added. Water (20 mL) was added after 1 hour followed by diethyl ether (20 mL). The organic layer was separated and the aqueous layer extracted with diethyl ether (2×20 mL). The combined extracts were dried with magnesium sulfate, filtered and the solvent removed. The crude product was chromatographed using 5% ethyl acetate in petroleum spirits to isolate the product as a yellow oil (2.34 g, 50%). 1H-nmr (CDCl3) δ 4.60 (2H), 6.30 (2H), 7.40 (5H), 7.70 (2H). 13C-nmr (CDCl3) δ 41.7, 114.2, 120.6, 128.0, 128.8, 129.4, 135.0, 189.0.

後処理

  1. additionOn completion of addition the resulting brown solution
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with diethyl ether (2×20 mL)
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe crude product was chromatographed

出典と根拠

ORDレコード
ord-0f464493d4fd4abda51f32c826789691
出典データセット
uspto-grants-2004_06
特許番号
US06747111B2

反応ノート

読み込み中…