Bromine → 2-Amino-7-bromo-6,7-dihydro-4H-cyclohepta[d]thiazol-8(5H)-one

HRID 1942997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942997
[NH2:1][C:2]1[S:3][C:4]2[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.[Br:13]Br>C(O)(=O)C>[NH2:1][C:2]1[S:3][C:4]2[C:11](=[O:12])[CH:10]([Br:13])[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 251308282-amino-4H,5H,6H,7H,8H-cyclohepta[d][1,3]thiazol-8-one

Produkt 1

HCID 251304942-Amino-7-bromo-6,7-dihydro-4H-cyclohepta[d]thiazol-8(5H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Compound 26z (1.96 g, 7.45 mmol; HBr salt form) in glacial acetic acid (70 mL) was treated dropwise with Br2 (421 uL, 8.2 mmol). The reaction mixture was stirred at room temperature for 30 min. The crude product was collected by filtration, washed with cold acetone, and dried to yield 27z which was used in the next step without purification (1.98 g, 78%). 1H NMR (600 MHz, 2 DMSO-d6): δ 8.71 (br s, 2H), 5.11 (dd, J=6.9 Hz, 3.3 Hz, 1H), 3.08-2.90 (m, 2H), 2.473 2.39 (m, 1H), 2.28-2.20 (m, 1H), 2.14 (dd, J=10.1 Hz, 2.3 Hz, 1H), 1.98-1.90 (m, 1H). MS (ESI) m/z [M+H]+ 260.92; [(M+2)+H]+ 262.88. 5 6

Aufarbeitung

  1. filtrationThe crude product was collected by filtration
  2. washwashed with cold acetone
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a47fab81615544edb52ed9dd64143ab0
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389736B2

Notizen zur Reaktion

Wird geladen…