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反応

Hydrochloric Acid → (Z)-4-azido-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one

HRID 324961

印刷プレビュー

反応式

HRID 324961 の反応式

F[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:15]/[C:16]1[NH:17][CH:18]=[CH:19][C:20]=1[O:21][CH3:22])/[C:5](=[O:14])[NH:6]2.C(N(C(C)C)CC)(C)C.C[Si]([N:36]=[N+:37]=[N-:38])(C)C.Cl>C1COCC1.C(O)C>[N:36]([C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:15]/[C:16]1[NH:17][CH:18]=[CH:19][C:20]=1[O:21][CH3:22])/[C:5](=[O:14])[NH:6]2)=[N+:37]=[N-:38]

参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric Acid

HCID 78378Azidotrimethylsilane

HCID 81531Diisopropylethylamine

HCID 15512601(Z)-1,3-Dihydro4-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one2 回

生成物 1

HCID 15512602(Z)-4-azido-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒

HCID 8028Tetrahydrofuran溶媒

実験手順

(Z)-1,3-Dihydro4-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one (6.60 g, 21.8 mmol) (Starting Material 3 above) was suspended in 330 mL of THF and 165 mL of ethanol. To this mixture was added diisopropylethylamine (56.9 ml, 326 mmol) (Aldrich) and trimethylsilyl azide (28.6 mL, 218 mmol) (Aldrich). The reaction mixture was heated at reflux overnight, and then poured into 2 L mixture of ice and 1 N HCl solution. The solid precipitate was filtered, washed with water and dried at 50° C. under high vacuum to give (Z)4-azido-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one as a dark red solid. (Yield 6.44 g, 90%)

後処理

temperatureThe reaction mixture was heated
temperatureat reflux overnight
filtrationThe solid precipitate was filtered
washwashed with water
customdried at 50° C. under high vacuum

出典と根拠

ORDレコード: ord-d1d8a156fd55474bbc1d18874cfc8f4e
出典データセット: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06221867B1

反応ノート

読み込み中…

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