Cyanamide → 2-Chloro-5-[(methylsulfinyl)methyl]pyridine

HRID 646628

反応式

HRID 646628 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9][CH3:10])=[CH:4][N:3]=1.N#CN.IC1C=CC=C(CC([O-])=[O:23])C=1CC([O-])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([CH3:10])=[O:23])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 9864CyanamideHCID 206703602-Chloro-5-[(methylthio)methyl]pyridineHCID 219456882-[2-(Carboxylatomethyl)-3-iodophenyl]acetate

生成物 1

HCID 592659452-Chloro-5-[(methylsulfinyl)methyl]pyridine収率 18.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of sulfide (A) (3.5 g, 17 mmol) and cyanamide (1.4 mg, 34 mmol) in CH2Cl2 (30 mL) at 0° C. was added iodobenzenediacetate (11.0 g, 34 mmol) all at once. The reaction was stirred for 30 min, then allowed to warm to room temperature overnight. The mixture was diluted with CH2Cl2 (50 mL) and washed with H2O. The aqueous layer was extracted with ethyl acetate (4×50 mL), and the combined organic layers were dried over MgSO4 and concentrated. The crude product was triturated with hexanes and purified by chromatography (chromatotron, 60% acetone/hexanes) to furnish the sulfilimine (B) as a yellow gum (0.60 g, 14%). IR (film) 3008, 2924, 2143, 1693 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.8 (s, 1H), 8.0 (d, 1H), 7.8 (d, 1H), 4.5 (d, 1H), 4.3 (d, 1H), 2.9 (s, 3H); LC-MS (ESI): mass calcd for C9H9F3N3S [M+H]+ 248.04. Found 248.

後処理

  1. washwashed with H2O
  2. extractionThe aqueous layer was extracted with ethyl acetate (4×50 mL)
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was triturated with hexanes
  6. custompurified by chromatography (chromatotron, 60% acetone/hexanes)

出典と根拠

ORDレコード
ord-d238ff45d17146fa960fba9dfb7beb5c
出典データセット
uspto-grants-2010_04
特許番号
US07705156B2

関連ノート

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