2-Chloro-1,4-naphthoquinone → N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide

HRID 1258379

反応式

HRID 1258379 の反応式
[Cl:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=O)[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[S:19]([NH2:22])(=[O:21])=[O:20]>C(OCC)(=O)C>[Cl:1][C:2]1[C:3](=[O:13])[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10](=[N:22][S:19]([C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)(=[O:21])=[O:20])[CH:11]=1

参加物

4

反応物 2

HCID 138912-Chloro-1,4-naphthoquinoneHCID 728812-Thiophenesulfonamide

生成物 1

HCID 697416N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide収率 55.9%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

385.2 mg 2-chloro-1,4-naphthoquinone (11) was mixed with 326.4 mg thiophene-2-sulfonamide in 15 ml dichloromethylene, to which at 0° C. was added 2 ml TiCl4 dichloromethylene solution followed by 613.3 μl. The mixture was heated at 60° C. with M.W. for 15 min and the black mixture was poured into 100 ml ethyl acetate. The insoluble was removed by filtrate through a pad of celite. The filtrate was concentrated and the residue was suspended in dichloromethylene. The brown insoluble stuff was removed by filtration and the filtrate was again concentrated to dryness. The residue was suspended in ethyl acteate/hexane (1:1) and the yellow solid was filtered. The solid was washed with ethyl acteate/hexane (1:1) and dried over vacuum affording title compound 377.7 mg (55.9%) as a yellow solid. When TiCl4.2THF and THF were used instead, the reaction afforded the title compound 522 mg (77.3%) as a yellow solid, m.p.: 167-169° C.

後処理

  1. customThe insoluble was removed by filtrate through a pad of celite
  2. concentrationThe filtrate was concentrated
  3. customThe brown insoluble stuff was removed by filtration
  4. concentrationthe filtrate was again concentrated to dryness
  5. filtrationthe yellow solid was filtered
  6. washThe solid was washed with ethyl acteate/hexane (1:1)
  7. customdried over vacuum

出典と根拠

ORDレコード
ord-2bcc240fbb1f45b79d13853668afa919
出典データセット
uspto-grants-2013_06
特許番号
US08466157B2

関連ノート

読み込み中…