Benzoyl chloride → HCID 58982138, Verbindung

HRID 1182494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182494
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)C(Cl)=O.C(Cl)(=O)C1C=CC=CC=1.Br[C:21]1[CH:39]=[CH:38][C:24]([C:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35]CC)=O)=[O:26])=[CH:23][CH:22]=1.C(CCCCCCC(OCC)=O)(=O)C1C=CC=CC=1.[NH2:59][OH:60].Cl>C(N(CC)CC)C>[OH:60][NH:59][C:33](=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][C:25]([C:24]1[CH:38]=[C:39]([C:10]2[CH:9]=[CH:8][CH:4]=[CH:3][CH:2]=2)[CH:21]=[CH:22][CH:23]=1)=[O:26]

Komponenten

7

Edukt 5

HCID 7412Benzoyl chlorideHCID 74377Benzoyl chloride, 3-bromo-HCID 443297Hydroxyamine hydrochlorideHCID 10934282Ethyl 8-oxo-8-phenyloctanoateHCID 11024292ETHYL 8-(4-BROMOPHENYL)-8-OXOOCTANOATE

Produkt 1

HCID 58982138HCID 58982138, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Following the procedure described in Example 18, step 1, 2, but substituting respectively 3-bromobenzoyl chloride for benzoyl chloride, the resulting ester was substituted for 49d in Example 67, step 1. Then, following the procedure described in Example 18, step 3, but substituting the final ester for ester 49a, the resulting acid was substituted in Example 14, step 3, using 1.1 equivalent of NH2OH.HCl and triethylamine each, to afford the title compound 131 in 35% yield. 1H NMR (300 MHz, CDCl3): δ 8.13 (s, 1H), 7.88-7.30 (m, 8H), 2.96 (br t, 2H), 2.17 (m, 2H), 1.77-1.58 (m, 4H), 1.35 (m, 4H). 13C NMR (75 MHz, CDCl3) δ623.93, 25.12, 28.71(2), 32.73, 38.48, 126.61, 126.88, 127.08, 127.72, 128.85, 128.99, 131.58, 137.30, 140.06, 141.57, 171.82, 200.75.

Quellen und Nachweise

ORD-Eintrag
ord-29d2ab9e06184fec8090fe2e5950ff90
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288567B2

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