Water → HCID 86751872, compound

HRID 725668Notes

Reaction equation

HRID 725668 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([C:22]2[CH:30]=[CH:29][C:28]([C:31]([O:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][O:47][C:48](=[O:51])[CH:49]=[CH2:50])=[CH:36][CH:35]=3)=[O:32])=[CH:27][C:23]=2[C:24]([OH:26])=[O:25])=[O:21])=[CH:15][CH:14]=1)(=[O:4])[CH:2]=[CH2:3].[N+:52]([C:55]1[CH:60]=[CH:59][C:58]([N:61]=[N:62][C:63]2[CH:76]=[CH:75][C:66]([O:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73]O)=[CH:65][CH:64]=2)=[CH:57][CH:56]=1)([O-:54])=[O:53].O>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]([C:22]2[CH:30]=[CH:29][C:28]([C:31]([O:33][C:34]3[CH:35]=[CH:36][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][O:47][C:48](=[O:51])[CH:49]=[CH2:50])=[CH:38][CH:39]=3)=[O:32])=[CH:27][C:23]=2[C:24]([O:26][CH2:73][CH2:72][CH2:71][CH2:70][CH2:69][CH2:68][O:67][C:66]2[CH:65]=[CH:64][C:63]([N:62]=[N:61][C:58]3[CH:57]=[CH:56][C:55]([N+:52]([O-:54])=[O:53])=[CH:60][CH:59]=3)=[CH:76][CH:75]=2)=[O:25])=[O:21])=[CH:17][CH:18]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 962WaterHCID 11427873HCID 11427873, compoundHCID 54071153HCID 54071153, compound

Product 1

HCID 86751872HCID 86751872, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.2 g of N,N'-dicyclohexyldicarbodiimide (DCC) was added at room temperature while stirring to a solution of 0.5 g of 2,5-bis[4-(6-acryloyloxyhexyloxy)phenylcarboxy]benzoic acid, 0.25 g of 6-[4-(4-nitrophenylazo)phenoxy]hexanol and 0.04 g of 4-dimethylaminopyridine (DMAP) in 25 ml of dichloromethane. The reaction mixture was stirred at room temperature overnight, poured into 100 ml of water and then extracted three times with 50 ml of dichloromethane each time. The organic phases were combined, washed twice with 100 ml of water each time, dried over magnesium sulphate, filtered and the filtrate was concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol 1:1) and two-fold recrystallization from acetone of the fractions which were pure according to thin-layer chromatography gave 0.4 g of 6-[4-(4-nitrophenylazo)phenoxy]hexyl 2,5-bis[4-(6-acryloyloxyhexyloxy)phenylcarboxy]benzoate; m.p. (C-N) 72° C., cl.p. (N-I) 127° C.

Workup

  1. extractionextracted three times with 50 ml of dichloromethane each time
  2. washwashed twice with 100 ml of water each time
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customChromatographic purification of the residue on silica gel
  7. customwith hexane/ethyl acetate (vol 1:1) and two-fold recrystallization from acetone of the fractions which

Sources & evidence

ORD record
ord-9731ad2a3c4749bcbeeed7e6601563f2
Source dataset
uspto-grants-1998_01
Patent number
US05707544

Reaction notes

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