Sodium Dithionite → 3-Amino-4-(2,5-dichlorophenoxy)benzonitrile

HRID 1184380

反応式

HRID 1184380 の反応式
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[N+:13]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.O>[NH2:13][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:5]=1[O:4][C:3]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:2]=1[Cl:1])[C:9]#[N:10]

参加物

5

反応物 2

HCID 24489Sodium DithioniteHCID 595489424-(2,5-Dichlorophenoxy)-3-nitrobenzonitrile

生成物 1

HCID 435182193-Amino-4-(2,5-dichlorophenoxy)benzonitrile収率 103.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

The coupled product 34 was reduced with sodium hydrosulfite ((49.76 g, 268.56 mmol) in a mixture of THF (200 mL) and water (100 mL). After the reaction was complete, THF was removed in vacuo. The product was precipitated out from the remaining reaction mixture, and was collected via vacuum filtration to yield compound 35 (12.961 g, 103.7% yield, 97.3% pure). 1H NMR (500 MHz, DMSO-d6): δ 7.64 (d, J=9 Hz, 1H), 7.31 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.13 (d, J=2 Hz, 1H), 7.08 (d, J=2 Hz, 1H), 6.93 (dd, J1=8 Hz, J2=2 Hz, 1H), 6.74 (d, J=8 Hz, 1H), 5.63 (s, 2H).

後処理

  1. customTHF was removed in vacuo
  2. customThe product was precipitated out from the remaining reaction mixture
  3. filtrationwas collected via vacuum filtration

出典と根拠

ORDレコード
ord-488923ef699e47e1a10240189a6e35f5
出典データセット
uspto-grants-2014_03
特許番号
US08669247B2

関連ノート

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