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Diethyl Ether → HCID 136366035, Verbindung

HRID 844897
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Reaktionsgleichung

Reaktionsgleichung von HRID 844897
[S:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=O)[C:2]#[N:3].[CH:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:25]2[NH:29][CH:28]=[CH:27][CH:26]=2)[C:20]2[NH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1.[NH4+:30].[Cl-].O([CH2:35][CH3:36])CC.C([C:39]1[C:45](=O)[C:44](Cl)=[C:43](Cl)[C:41](=O)[C:40]=1[C:49]#N)#N>C(#N)C>[C:40]1([C:49]2[C:23]3[CH:22]=[CH:21][C:20]([N:24]=3)=[C:8]([C:7]3[CH:10]=[CH:11][CH:12]=[C:5]([CH2:4][S:1][C:2]#[N:3])[CH:6]=3)[C:28]3[NH:29][C:25]([C:19]([C:16]4[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=4)=[C:20]4[N:24]=[C:23]([C:15]([C:36]5[CH:35]=[CH:16][CH:19]=[CH:25][CH:26]=5)=[C:14]5[NH:30][C:17]=2[CH:18]=[CH:13]5)[CH:22]=[CH:21]4)=[CH:26][CH:27]=3)[CH:39]=[CH:45][CH:44]=[CH:43][CH:41]=1
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Komponenten

7

Edukt 5

HCID 3283Diethyl EtherHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 25517Ammonium ChlorideHCID 43275135-PhenyldipyrromethaneHCID 22061823HCID 22061823, Verbindung

Produkt 1

HCID 136366035HCID 136366035, Verbindung
Ausbeute 9,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 316 mg of m-(thiocyanatomethyl)benzaldehyde (10, 1.8 mmol), 396 mg of 5-phenyldipyrromethane (Lee and Lindsey (1994) Tetrahedron, 50: 11427-11440, Littler et al. (1999) J. Org. Chem., 64: 1391-1396) (1.8 mmol) and 1.07 g of NH4Cl (20.0 mmol) in 200 mL of acetonitrile was purged with argon for 30 min. Under stirring at ambient temperature 23 μL of BF3.O(Et)2 (26 mg, 0.18 mmol) was added. Soon the solution turned to yellow and later to dark red. After 6.5 h, 607 mg of DDQ (2.7 mmol) was added. After 1 h the reaction was quenched with 0.5 mL of TEA (365 g, 3.6 mmol). The solvents were removed under reduced pressure. Purification was done by column chromatography over two flash silica gel columns with different solvent mixtures: (column 1) ether/hexanes (3:1) and (column 2) CH2Cl2/hexanes (gradient, start: 1:1). Two fractions of dark purple solids were obtained. I: 12 mg 10,15,20-triphenyl-5-[m-(thiocyanatomethyl)phenyl]porphyrin (17.5 μmol, 2% yield). II: 44 mg of the title compound (58.1 μmol, 7% yield). IR (neat): {tilde over (ν)}=2921 (s, CH), 2850 (m, CH), 2154 (m, CN), 1597 (m, arom. C═C), 1471 (s), 1348 (m), 1206 (m), 1181 (w), 1097 (w), 973 (s), 898 (w), 743 (s), 691 (s), 623 (s); 1H NMR (300.5 MHz, CDCl3): δ=−2.811 (s, 2H, NH), 4.57 (s, 4H, CH2), 7.71-7.83 (m, 11H, ArH), 8.17-8.25 (m, 8H, ArH), 8.84 (d, 4H, β-pyrrole, 3J=5.1 Hz), 8.88 (d, 4H, β-pyrrole); LD-MS calcd av mass 756.9, obsd 757.4, 699.2 [M+−SCN], 641.0 [M+−2 SCN]; FAB-MS obsd 756.2172, calcd exact mass 756.2130 (C48H32N6S2); λabs (toluene) 420, 514, 549, 590, 647, 657 nm.

Aufarbeitung

  1. customwas purged with argon for 30 min
  2. customThe solvents were removed under reduced pressure
  3. customPurification
  4. customTwo fractions of dark purple solids were obtained

Quellen und Nachweise

ORD-Eintrag
ord-6cdfc3b8475448a599534d8b061a6ca4
Quelldatensatz
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06381169B1

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