Water → HCID 86751873, compound

HRID 725669Notes

Reaction equation

HRID 725669 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([C:37]2[CH:45]=[CH:44][C:43]([C:46]([O:48][C:49]3[CH:54]=[CH:53][C:52]([O:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][O:62][C:63](=[O:66])[CH:64]=[CH2:65])=[CH:51][CH:50]=3)=[O:47])=[CH:42][C:38]=2[C:39]([OH:41])=[O:40])=[O:36])=[CH:30][CH:29]=1)(=[O:19])[CH:17]=[CH2:18].[N+:67]([C:70]1[CH:75]=[CH:74][C:73]([N:76]=[N:77][C:78]2[CH:94]=[CH:93][C:81]([C:82]([O:84][C:85]3[CH:90]=[CH:89][C:88]([CH2:91]O)=[CH:87][CH:86]=3)=[O:83])=[CH:80][CH:79]=2)=[CH:72][CH:71]=1)([O-:69])=[O:68].O>CN(C)C1C=CN=CC=1.ClCCl>[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][C:35]([C:37]2[CH:45]=[CH:44][C:43]([C:46]([O:48][C:49]3[CH:50]=[CH:51][C:52]([O:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][O:62][C:63](=[O:66])[CH:64]=[CH2:65])=[CH:53][CH:54]=3)=[O:47])=[CH:42][C:38]=2[C:39]([O:41][CH2:91][C:88]2[CH:89]=[CH:90][C:85]([O:84][C:82](=[O:83])[C:81]3[CH:80]=[CH:79][C:78]([N:77]=[N:76][C:73]4[CH:74]=[CH:75][C:70]([N+:67]([O-:69])=[O:68])=[CH:71][CH:72]=4)=[CH:94][CH:93]=3)=[CH:86][CH:87]=2)=[O:40])=[O:36])=[CH:32][CH:33]=1)(=[O:19])[CH:17]=[CH2:18]

Participants

7

Reactant 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 19708336HCID 19708336, compoundHCID 54071153HCID 54071153, compound

Product 1

HCID 86751873HCID 86751873, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.2 g of N,N'-dicyclohexylcarbodiimide is added at room temperature while stirring to a solution of 0.6 g of 2,5-bis[4-(6-acryloyloxyhexyloxy)phenylcarboxy]benzoic acid, 0.4 g of (4-[4-(4-nitrophenylazo)benzoyloxy]phenyl)methanol and 0.04 g of 4-dimethylaminopyridine in 20 ml of dichloromethane. The reaction as mixture is 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 are combined, washed twice with 100 ml of water each time, dried over magnesium sulphate, filtered and the filtrate is 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 are pure according to thin-layer chromatography gives 0.4 g of (4-[4-(4-nitrophenylazo)benzoyloxy]phenyl)methyl 2,5-bis[4-(6-acryloyloxyhexyloxy)phenylcarboxy]benzoate.

Workup

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

Sources & evidence

ORD record
ord-f98a3236ae784fdd8bbe5ab1ef6404aa
Source dataset
uspto-grants-1998_01
Patent number
US05707544

Reaction notes

Loading…