Water → HCID 21072080, compound

HRID 1372810Notes

Reaction equation

[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)(=[O:4])[CH:2]=[CH2:3].C([N:24]([CH2:27][CH3:28])CC)C.CO[CH2:31][CH2:32][O:33][CH3:34].CS(Cl)(=O)=O.[OH2:40]>CN(C)C1C=CN=CC=1>[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]([C:17]([O:19][C:13]2[CH:21]=[CH:31][C:32]([O:33][C:34](=[O:40])[C:8]3[CH:9]=[CH:10][C:28]([C:27]#[N:24])=[CH:6][CH:7]=3)=[CH:15][CH:14]=2)=[O:18])=[CH:20][CH:21]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: -30 °C

Procedure

A reaction flask was charged with 11.08 g (0.038 moles) of 4-{[6-(acryloyloxy)hexyl]oxy}benzoic acid, 7.67 g (0.076 moles) of triethylamine and 110 g of ethylene glycol dimethyl ether. The solution was cooled to −30° C., and 4.34 g (0.038 moles) of methane sulfonyl chloride was added. After maintaining stirring at −30° C. for one additional hour, 9.09 g (0.038 moles) of intermediate 6 and 0.46 g (0.004 moles) of 4-(dimethylamino)pyridine were added. The resulting mixture was then warmed to room temperature, and then to 50° C. for three hours. Finally, the mixture was cooled to room temperature and diluted with 300 ml of water. The crude product was collected by filtration and washed with water. The product, 7, was purified by recrystallization from ethanol.

Workup

temperatureAfter maintaining
additionwere added
temperatureThe resulting mixture was then warmed to room temperature
temperatureFinally, the mixture was cooled to room temperature
filtrationThe crude product was collected by filtration
washwashed with water
customThe product, 7, was purified by recrystallization from ethanol

Sources & evidence

ORD record: ord-bdf0e0d0258241deb9cd575789f0570b
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160586B2

Reaction notes

Loading…