Thiophosgene → 3,6-Dichloro-2-isothiocyanatopyridine

HRID 1177510ノート

反応式

HRID 1177510 の反応式
[Cl:1][C:2]1[C:3]([NH2:9])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:16](Cl)(Cl)=[S:17]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([N:9]=[C:16]=[S:17])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 10040ThiophosgeneHCID 10340Sodium CarbonateHCID 36134253,6-Dichloropyridin-2-amine

生成物 1

HCID 866387173,6-Dichloro-2-isothiocyanatopyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
55 °C

実験手順

A mixture of 3,6-dichloropyridin-2-amine (0.772 g, 4.74 mmol), sodium carbonate (2.01 g, 18.9 mmol), and thiophosgene (0.726 mL, 9.47 mmol) in 6 mL DCM was heated to 55° C. in a sealed tube for 36 h. The reaction was filtered through a frit, rinsing with DCM, and the material was adsorbed onto 6 g silica gel and dried. The material was purified by silica gel chromatography, 40 g, 0-100% EA/hexanes to give 3,6-dichloro-2-isothiocyanatopyridine. 1H NMR (400 MHz, DMSO-d6) 8 ppm 8.19 (d, J=8.5 Hz, 1 H), 7.59 (d, J=9.5 Hz, 1 H).

後処理

  1. filtrationThe reaction was filtered through a frit
  2. washrinsing with DCM
  3. customdried
  4. customThe material was purified by silica gel chromatography, 40 g, 0-100% EA/hexanes

出典と根拠

ORDレコード
ord-a27c9952527343d798d4d78fdd80ee65
出典データセット
uspto-grants-2010_11
特許番号
US07842685B2

反応ノート

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