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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
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Water → 2,5-Bis(2-octyldodecyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

HRID 468708
ノート
印刷プレビュー

反応式

HRID 468708 の反応式
O=[C:2]1[C:6]2=[C:7]([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)[NH:8][C:9](=[O:10])[C:5]2=[C:4]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[NH:3]1.[C:21]([O-:24])([O-])=O.[K+].[K+].[CH2:27]([CH:35]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:36]Br)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].O>CN(C)C=O>[CH2:27]([CH:35]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:2][N:3]1[C:4]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[C:5]2[C:6](=[C:7]([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)[N:8]([CH2:36][CH:35]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C:9]2=[O:10])[C:21]1=[O:24])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 231487459-(Bromomethyl)nonadecaneHCID 1785175291,4-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione

生成物 1

HCID 670424062,5-Bis(2-octyldodecyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione収率 54%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
120 °C

実験手順

In a three-neck, oven dried, 250 ml round bottom flask, 2,5-dihydro-1,4-dioxo-3,6-dithienylpyrrolo[3,4-c]-pyrrole (2), (7.0 g. 23.30 mmol) and anhydrous K2CO3 (8.95 g, 69.91 mmol) were dissolved in 250 ml of anhydrous N,N-dimethylformamide (DMF), and heated to 120° C. under argon for 1 h. 2-octyl-1-dodecylbromide (25.27 g, 69.91 mmol) was then added dropwise, and the reaction mixture was further stirred and heated overnight at 130° C. The reaction mixture was cooled to room temperature and then poured into water and stirred for 30 minutes. The product was extracted with chloroform, then successively washed with water, and dried over MgSO4. Removal of the solvent afforded the crude product which was then purified using column chromatography on silica gel using a mixture of hexane and chloroform as eluent, giving a purple solid (11.0 g, 54%). 1H NMR (CDCl3): (0.87 (t, 12H), 1.13-1.45 (m, 64H), 1.89 (s, 2H), 4.00 (d, 4H), 7.26 (d, 2H), 7.52 (d, 2H), 8.87 (d, 2H). MS (MALDI-TOF) m/z 860.63 (M). calcd. for C54H88N2O2S2=860.25.

後処理

  1. customIn a three-neck, oven dried
  2. temperatureheated overnight at 130° C
  3. temperatureThe reaction mixture was cooled to room temperature
  4. stirringstirred for 30 minutes
  5. extractionThe product was extracted with chloroform
  6. washsuccessively washed with water
  7. dry with materialdried over MgSO4
  8. customRemoval of the solvent
  9. customafforded the crude product which
  10. customwas then purified
  11. additiona mixture of hexane and chloroform as eluent

出典と根拠

ORDレコード
ord-05907aa3aad04f1d92365932685da392
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08624232B2

反応ノート

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