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Diethyl Ether → HCID 136366035, compound

HRID 2111447
Notes
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Reaction equation

HRID 2111447 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

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

Product 1

HCID 136366035HCID 136366035, compound
Yield 9.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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 (v)}=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+-2SCN]; FAB-MS obsd 756.2172, calcd exact mass 756.2130 (C48H32N6S2); λabs (toluene) 420, 514, 549, 590, 647, 657 nm.

Workup

  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

Sources & evidence

ORD record
ord-d9545a2f7ccc4fb9ab08ba259c0d41de
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07518905B2

Reaction notes

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