Hydrogen Sulfide → 1,9-dimethyl-10H-phenothiazine

HRID 408108

反応式

HRID 408108 の反応式
[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14].[S].II.[SH2:19]>ClC1C=CC=CC=1Cl>[CH3:14][C:9]1[C:8]2[NH:7][C:2]3[C:3](=[CH:4][CH:5]=[CH:6][C:1]=3[CH3:15])[S:19][C:13]=2[CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 402Hydrogen SulfideHCID 807IodineHCID 136423Benzenamine, 2-methyl-N-(2-methylphenyl)-HCID 5362487Sulfur

生成物 1

HCID 674644911,9-dimethyl-10H-phenothiazine収率 15%

試薬・触媒・溶媒 1

HCID 72391,2-Dichlorobenzene溶媒

反応条件

温度
180 °C

実験手順

To a reaction vessel were combined di(2-tolyl)amine (11.7 g, 59.3 mmol), elemental sulfur (3.9 g, 121.65 mmol, 2 eq.), crushed iodine (0.44 g, 1.73 mmol, 3 mol %) followed by o-dichlorobenzene (22 mL). Added an outlet to a dilute bleach solution (for hydrogen sulfide evolution) then put under argon. Refluxed at 180° C. for 4 h and removed solvent under reduced pressure. Purified by column chromatography with 2.0% ethyl acetate/98% hexane to obtain the desired product as white crystals (2 g, 8.8 mmol, 15% yield). Alternatively, the reaction was cooled to about 60° C. then hexane was added for extraction. Repeated hot hexane extractions of reaction until the product was no longer obtained in residue (about four times). Combined hexane extractions and concentrated in vacuo. Purified resulting residue either through repeated hot acetone/isopropanol crystallizations (or triturations) or flash column chromatography using 2% ethyl acetate/98% hexane to obtain product as white crystals (2.92 g, 12.8 mmol, 28% yield).

後処理

  1. customTo a reaction vessel were combined
  2. customremoved solvent under reduced pressure
  3. customPurified by column chromatography with 2.0% ethyl acetate/98% hexane

出典と根拠

ORDレコード
ord-3176436d63ff43128bda32f193290546
出典データセット
uspto-grants-2014_06
特許番号
US08759336B2

関連ノート

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