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Bromine → (z)-Methyl 4-(7-bromo-2-oxo-2,3-dihydro-1h-thieno[2,3-e][1,4]diazepin-5-yl)benzoate

HRID 1946654
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1946654
[O:1]=[C:2]1[NH:8][C:7]2[S:9][CH:10]=[CH:11][C:6]=2[C:5]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)=[N:4][CH2:3]1.[Br:22]Br>N1C=CC=CC=1>[Br:22][C:10]1[S:9][C:7]2[NH:8][C:2](=[O:1])[CH2:3][N:4]=[C:5]([C:12]3[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=3)[C:6]=2[CH:11]=1
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Komponenten

4

Edukt 2

HCID 24408BromineHCID 136106241(Z)-methyl 4-(2-oxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-5-yl)benzoate

Produkt 1

HCID 136106240(z)-Methyl 4-(7-bromo-2-oxo-2,3-dihydro-1h-thieno[2,3-e][1,4]diazepin-5-yl)benzoateAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a 20 mL dram screw-cap vial with septum was dissolved compound 493 (0.140 g, 0.466 mmol) in pyridine (3 mL) to give an orange solution. The mixture was cooled to 0° C. and bromine (0.029 mL, 0.559 mmol) was added dropwise. The reaction mixture was left to stir at 0° C. for 1 hour. The mixture was quenched with saturated thiosulfate solution and extracted with ethyl acetate. The organic layer was washed several times with water, then brine, dried over magnesium sulfate, filtered and evaporated. The residue was suspended in ether and filtered to afford title compound 494 (101 mg, 57%) as a tan solid. MS (m/z): 379.33 (M+H).

Aufarbeitung

  1. customIn a 20 mL dram screw-cap vial with septum
  2. customto give an orange solution
  3. waitThe reaction mixture was left
  4. customThe mixture was quenched with saturated thiosulfate solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed several times with water
  7. dry with materialbrine, dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-cb7ce32af1764a728306eed025037ae9
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08399452B2

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