Water → HCID 178454692, compound

HRID 555199Notes

Reaction equation

HRID 555199 reaction equation
[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](/[N:34]=[N:35]/[C:36]2[CH:41]=[CH:40][C:39](/[N:42]=[N:43]/[C:44]3[CH:49]=[CH:48][C:47](/[N:50]=[N:51]/[C:52]4[C:61]5[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=5)[C:55]([OH:62])=[CH:54][CH:53]=4)=[CH:46][CH:45]=3)=[CH:38][CH:37]=2)=[CH:26][CH:25]=1.[OH2:63]>C1COCC1.C(N(CC)CC)C.CN(C1C=CN=CC=1)C>[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([O:62][C:55]2[C:56]3[C:61](=[CH:60][CH:59]=[CH:58][CH:57]=3)[C:52](/[N:51]=[N:50]/[C:47]3[CH:46]=[CH:45][C:44](/[N:43]=[N:42]/[C:39]4[CH:38]=[CH:37][C:36](/[N:35]=[N:34]/[C:27]5[C:28]6[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=6)[C:24]([O:23][C:18](=[O:19])[C:17]6[CH:21]=[CH:22][C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[CH:15][CH:16]=6)=[CH:25][CH:26]=5)=[CH:41][CH:40]=4)=[CH:49][CH:48]=3)=[CH:53][CH:54]=2)=[O:19])=[CH:21][CH:22]=1)(=[O:63])[C:2]([CH3:4])=[CH2:3]

Participants

7

Reactant 3

HCID 962WaterHCID 37303444-{[6-(Methacryloyloxy)hexyl]oxy}benzenecarboxylic acidHCID 178516259HCID 178516259, compound

Product 1

HCID 178454692HCID 178454692, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-30 °C

Procedure

1.28 g of 4-{[6-(methacryloyloxy)hexyl]oxy}benzoic acid (4.20 mM) were dissolved in 30 ml of THF and 4.00 g of triethylamine (40.00 mM). The solution was cooled to −30° C. and 0.48 g of methansulfochloride (4.20 mM) were added. The mixture was stirred for 0.5 h at this temperature, then 1.04 g of bis{4-[(E)-(4-hydroxy-1-naphthyl)diazenyl]phenyl}-(E)-diazene (2.00 mM) were added at once, followed by 50 mg of DMAP. The reaction mixture was stirred for 1 h at −30° C. and was allowed to warm to room temperature while stirred overnight. The next day, the reaction mixture was poured onto 200 ml of water, the resulting suspension was stirred for 10 min. and the solids were filtered off, washed with water and dried. The resulting orange powder was boiled for 1 h in 25 ml of ethanol, cooled to room temperature and the solid was filtered off, washed with ethanol and dried to give 1.60 g (1.46 mM, 73%) of bis{4-((E)-{4-[(4-{[6-(methacryloyloxy)hexyl]oxy}benzoyl)oxy]-1-naphthyl}diazenyl)-phenyl}-(E)-diazene as orange crystals; λmax=428 nm, ε=52000 (THF).

Workup

  1. addition0.48 g of methansulfochloride (4.20 mM) were added
  2. stirringThe reaction mixture was stirred for 1 h at −30° C.
  3. temperatureto warm to room temperature
  4. stirringwhile stirred overnight
  5. stirringthe resulting suspension was stirred for 10 min.
  6. filtrationthe solids were filtered off
  7. washwashed with water
  8. customdried
  9. waitThe resulting orange powder was boiled for 1 h in 25 ml of ethanol
  10. temperaturecooled to room temperature
  11. filtrationthe solid was filtered off
  12. washwashed with ethanol
  13. customdried

Sources & evidence

ORD record
ord-701e509563ef47d182cadae8f344a1ec
Source dataset
uspto-grants-2011_11
Patent number
US08053039B2

Reaction notes

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