Triethylamine → HCID 18979551, compound

HRID 2392585Notes

Reaction equation

HRID 2392585 reaction equation
C(N([CH2:6][CH3:7])CC)C.CS(Cl)(=O)=O.C(OCCCCCCCCOC1C=CC(C(O[C:36]2[CH:37]=[C:38]([CH:42]=[CH:43][C:44]=2[O:45][C:46]([C:48]2[CH:53]=[CH:52][C:51]([O:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][O:63][C:64](=[O:67])[CH:65]=[CH2:66])=[CH:50][CH:49]=2)=[O:47])[C:39]([OH:41])=[O:40])=O)=CC=1)(=O)C=C.[F:68][C:69]1[CH:76]=[C:75]([OH:77])[CH:74]=[CH:73][C:70]=1[C:71]#[N:72]>O1CCCC1.CN(C)C1C=CN=CC=1.O>[C:64]([O:63][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][O:54][C:51]1[CH:50]=[CH:49][C:48]([C:46]([O:45][C:44]2[CH:43]=[CH:42][C:38]([C:39]([O:41][C:76]3[C:69]([F:68])=[C:70]([CH:73]=[CH:74][C:75]=3[O:77][C:39]([C:38]3[CH:42]=[CH:43][C:44]([O:45][C:46]([C:48]4[CH:53]=[CH:52][C:51]([O:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][O:63][C:64](=[O:67])[CH:6]=[CH2:7])=[CH:50][CH:49]=4)=[O:47])=[CH:36][CH:37]=3)=[O:40])[C:71]#[N:72])=[O:40])=[CH:37][CH:36]=2)=[O:47])=[CH:53][CH:52]=1)(=[O:67])[CH:65]=[CH2:66]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 18979541HCID 18979541, compound

Product 1

HCID 18979551HCID 18979551, compoundYield 456.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-25 °C

Procedure

0.9 g of triethylamine and then 0.5 g of methanesulphonyl chloride were added dropwise at -25° C. while stirring to a solution of 0.4 g of 3,4-bis(4-[8-acryloyloxyoctyloxy]phenylcarbonyloxy)benzoic acid in 40 ml of tetrahydrofuran. The reaction mixture was stirred at -25° C. for 1 hour, then treated with 0.06 g of 2-fluoro-4-hydroxybenzonitrile and 0.05 g of 4-(dimethylamino)pyridine in 40 ml of tetrahydrofuran, stirred at room temperature overnight, poured into 100 ml of water and then extracted three times with 50 ml of diethyl ether 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 cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from ethyl alcohol of the fractions which were pure according to thin-layer chromatography gave 1.2 g of 3,4-bis[4-(4-[8-acryloyloxyoctyloxy]phenylcarbonyloxy)phenylcarbonyloxy]-2-fluorobenzonitrile; m.p. (C-I) 85° C., cl.p. (N-I) 3° C.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionextracted three times with 50 ml of diethyl ether each time
  3. washwashed twice with 100 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customChromatographic purification of the residue on silica gel
  8. customwith cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from ethyl alcohol of the fractions which

Sources & evidence

ORD record
ord-b04af408185a438cb2d4c4109b511d10
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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