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Cesium carbonate → HCID 86684833, Verbindung

HRID 595143
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 595143
[NH:1]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][C:7]3=[CH:6][C:5]=2[C:4](=[O:21])[CH:3]=[CH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].F[C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][C:30]=1[F:38]>CN(C=O)C.CC#N>[F:38][C:30]1[CH:31]=[C:32]([N+:35]([O-:37])=[O:36])[CH:33]=[CH:34][C:29]=1[O:21][C:4]1[C:5]2[CH:6]=[C:7]3[O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][C:8]3=[CH:9][C:10]=2[N:1]=[CH:2][CH:3]=1
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Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 739778531,4,7,10-Tetraoxacyclododecino[2,3-g]quinolin-15(12h)-one, 2,3,5,6,8,9-hexahydro-

Produkt 1

HCID 86684833HCID 86684833, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228Dimethylformamide
Lösungsmittel
2×
HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a round bottom flask equipped with a magnetic stir bar was added 7,8,10,11,13,14-Hexahydro-1H-6,9,12,15-tetraoxa-1-aza-cyclododeca[b]naphthalen-4-one (12.2 g, 43.3 mmol, 1.0 eq.), acetonitrile (150 ml), DMF (150 ml) and cesium carbonate (28.2 g, 86.5 mmol, 2.0 eq). The mixture was stirred at room temperature for 30 minutes at which time 1,2-difluoro-4-nitro-benzene (7.57 g, 47.6 mmoL, 1.1 eq) was added over a 10 minute period. After 2 hours the reaction was complete at which time 75% of the MeCN and DMF were removed and the resulting solution was poured over into ice water. The solid was filtered and dried and further columned with a biotage system. The eluent was 1:3 ethyl acetate/hexane. Removal of the solvent afforded 4-(2-Fluoro-4-nitro-phenoxy)-7,8,10,11,13,14-hexahydro-6,9,12,15-tetraoxa-1-aza-cyclodo-deca[b]naphthalene as a pale green solid (7.4 g, 41% yield). 1HNMR (400 MHz, DMSO): 8.58 (s, 1H), 7.80 (s, 1H), 7.50 (s, 1H), 7.04 (t, 1H), 6.88 (m, 1H), 6.50 (m, 2H), 4.35 (s, 4H), 3.87 (d, 4H), 3.62 (s, 4H). LC/MS Calcd for (M+H)+431.4. found 431.5.

Aufarbeitung

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. additionwas added over a 10 minute period
  3. customwere removed
  4. additionthe resulting solution was poured over into ice water
  5. filtrationThe solid was filtered
  6. customdried
  7. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-9fcdc2257ad94827bb464879441d3604
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242991B2

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