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

HRID 1946848

반응식

HRID 1946848 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-a93c0b4c1d0f40f3a7e155e3a649ee78
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399456B2

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