Benzoyl chloride, 3,4-dichloro- → 1-(3,4-Dichlorobenzoyl)indoline-5-sulfonamide

HRID 528825

Reaktionsgleichung

Reaktionsgleichung von HRID 528825
C1(C(N2C3C(=CC(S(N)(=O)=O)=CC=3)CC2)=O)CCCCC1.[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:28][CH:29]=2)[CH2:24][CH2:23]1.[Cl:35][C:36]1[CH:37]=[C:38]([CH:42]=[CH:43][C:44]=1[Cl:45])[C:39](Cl)=[O:40]>>[Cl:35][C:36]1[CH:37]=[C:38]([CH:42]=[CH:43][C:44]=1[Cl:45])[C:39]([N:22]1[C:30]2[C:25](=[CH:26][C:27]([S:31]([NH2:34])(=[O:32])=[O:33])=[CH:28][CH:29]=2)[CH2:24][CH2:23]1)=[O:40]

Komponenten

4

Edukt 3

HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 80272522,3-dihydro-1H-indole-5-sulfonamide2×HCID 606987421-(Cyclohexanecarbonyl)indoline-5-sulfonamide

Produkt 1

HCID 710607641-(3,4-Dichlorobenzoyl)indoline-5-sulfonamideAusbeute 36,3 %

Versuchsvorschrift

Following a procedure analogous to that for the synthesis of Intermediate 55, indoline-5-sulfonamide (Intermediate 54A, 195 mg, 0.98 mmol) and 3,4-dichlorobenzoyl chloride (412 mg, 1.97 mmol) were converted to the title compound (132 mg, 36%) after purification using preparative HPLC. 1H NMR (DMSO-d6) δ 7.92 (d, J=1.1 Hz, 1H), 7.78 (d, J=8.1 Hz, 1H), 7.71-7.61 (m, 3H), 7.26 (s, 2H), 4.07 (t, J=8.3 Hz, 2H), 3.16 (t, J=8.2 Hz, 2H); MS(ESI+) m/z 370.8 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-eba422339fb24e8b99caeb21989720c3
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346795B2

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