Boron tribromide → n-[5-Benzyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3-hydroxy-benzamide

HRID 556075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 556075
[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=2)=[N:10][C:9]=1[C:24]1[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[N:10][C:9]=1[C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 25134Boron tribromideHCID 57991616N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3-methoxy-benzamide

Produkt 1

HCID 57991627n-[5-Benzyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3-hydroxy-benzamideAusbeute 65 %

Versuchsvorschrift

A procedure similar to that in Example 7 was used. N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3-methyoxy-benzamide prepared in Example 42 and boron tribromide were used as starting materials. The obtained crude product was recrystallized with acetone to give a product as a white solid in a yield of 65.0%, mp: 233-234 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.23 (2H, s, CH2), 6.83 (2H, d, J=7.28 Hz, ArH), 6.98˜7.02 (1H, m, ArH), 7.22˜7.35 (6H, m, ArH), 7.40 (1H, s, ArH), 7.46 (2H, d, J=7.28 Hz, ArH), 7.52 (1H, d, J=7.56 Hz, ArH), 9.50 (1H, br, OH), 12.50 (1H, br, CONH); EI-MS m/e (%): 402.1 (M+, 83), 121.0 (100); HREI-MS Calcd. for C23H18N2O3S: 402.1038, found: 402.1042.

Aufarbeitung

  1. customThe obtained crude product
  2. customwas recrystallized with acetone

Quellen und Nachweise

ORD-Eintrag
ord-9f389f392fa641ab89aae8c0e009f5f2
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053581B2

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