Boron tribromide → HCID 57991607, compound

HRID 556077Notes

Reaction equation

HRID 556077 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][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][C:18]([OH:21])=[CH:17][CH:16]=2)=[N:10][C:9]=1[C:24]1[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 57991604N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-4-methoxy-benzamide

Product 1

HCID 57991607HCID 57991607, compoundYield 67.9%

Procedure

A procedure similar to that in Example 7 was used. N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-4-methyoxy-benzamide prepared in Example 27 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 67.9%, mp: 254-255 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.20 (2H, s, CH2), 6.84 (4H, t, J=7.80 Hz, ArH), 7.20˜7.28 (3H, m, ArH), 7.33 (2H, t, J=8.08 Hz, ArH), 7.47 (2H, d, J=8.64 Hz, ArH), 7.97 (2H, d, J=8.60 Hz, ArH), 9.61 (1H, s, OH), 10.29 (1H, s, OH), 12.34 (1H, s, CONH); EI-MS m/e (%): 402.0 (M+, 82), 282.1 (74), 121.0 (100); HREI-MS Calcd. for C23H18N2O3S: 402.1038. found: 402.1027.

Workup

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

Sources & evidence

ORD record
ord-643a8c69ae9541e792458dc9fdcdbf86
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

Loading…