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

HRID 408108

반응식

HRID 408108 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 674644911,9-dimethyl-10H-phenothiazine수율 15%

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매

반응 조건

온도
180 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3176436d63ff43128bda32f193290546
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759336B2

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