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

HRID 646628

반응식

HRID 646628 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d238ff45d17146fa960fba9dfb7beb5c
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705156B2

연결된 노트

불러오는 중…