Water → Di-[4-(2,2':6',2'')terpyridin-4'-yl-benzyl]-4,4'-azobis(4-cyanovalerate)

HRID 2218489

Reaction equation

HRID 2218489 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:12]=[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:10]=2)=[CH:5][CH:4]=1.[N:27]([C:38]([C:45]#[N:46])([CH3:44])[CH2:39][CH2:40][C:41]([OH:43])=[O:42])=[N:28][C:29]([C:36]#[N:37])([CH3:35])[CH2:30][CH2:31][C:32]([OH:34])=[O:33].C([O-])([O-])=O.[Cs+].[Cs+].O>CC(C)=O>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][O:42][C:41](=[O:43])[CH2:40][CH2:39][C:38]([N:27]=[N:28][C:29]([C:36]#[N:37])([CH3:35])[CH2:30][CH2:31][C:32]([O:34][CH2:2][C:3]3[CH:4]=[CH:5][C:6]([C:9]4[CH:10]=[C:11]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=5)[N:12]=[C:13]([C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=5)[CH:14]=4)=[CH:7][CH:8]=3)=[O:33])([C:45]#[N:46])[CH3:44])=[CH:4][CH:5]=2)[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 929384,4-Azobis(4-cyanovaleric acid)HCID 131532744'-(4-Bromomethylphenyl)-2,2':6',2''-terpyridine

Product 1

HCID 59015046Di-[4-(2,2':6',2'')terpyridin-4'-yl-benzyl]-4,4'-azobis(4-cyanovalerate)Yield 46.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A reaction mixture of 4′-(4-bromomethylphenyl)-2,2′:6′,2″-terpyridine (1.500 g, 3.729 mmol), 4,4′-azobis(4-cyanopentanoic acid) (500 mg, 1.7839 mmol), Cs2CO3 (750 mg, 2.302 mmol), 1.0 ml of water and 100 ml of acetone was stirred vigorously at room temperature for 5 days. The solvents were removed under vacuum, and CH2Cl2 was added. The precipitate was filtered off. The filtrate was evaporated to dryness under vacuum, and then 300 ml of CH2Cl2-hexane mixture solvents (1:12, v/v) was added. The precipitate was filtered, and dried, and further purified by column chromatography (Al2O3) using ethyl acetate-hexane (3:2, v/v) as eluent to give pure product (0.763 g, 46%). 1H-NMR (CDCl3): δ=8.64 (m, 12H), 7.85 (m, 8H), 7.47 (m, 4H), 7.30 (m, 4H), 5.20 (s, 4H, —CH2—O—C(O)—), 2.65-2.48(m,8H, —OOC—CH2CH2—), 1.69(m, 6H, =N—C(CN)—CH3). HRMS (TOF): calculated for C56H47N10O4[(M+H)+] m/z=923.3782, found m/z=923.3759 Fluorescent Spectral Properties: λex=320 nm, λem=380 nm.

Workup

  1. customThe solvents were removed under vacuum, and CH2Cl2
  2. additionwas added
  3. filtrationThe precipitate was filtered off
  4. customThe filtrate was evaporated to dryness under vacuum
  5. addition300 ml of CH2Cl2-hexane mixture solvents (1:12, v/v) was added
  6. filtrationThe precipitate was filtered
  7. customdried
  8. customfurther purified by column chromatography (Al2O3)

Sources & evidence

ORD record
ord-2193dc8de7224420acf37cafea359a79
Source dataset
uspto-grants-2008_08
Patent number
US07411053B2

Linked notes

Loading…