Boron tribromide → HCID 57991582, compound

HRID 556071Notes

Reaction equation

HRID 556071 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][CH3:22])=[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]([O:21][CH3:22])=[CH:17][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

Participants

3

Reactant 2

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

Product 1

HCID 57991582HCID 57991582, compoundYield 41.3%

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 41.3%, mp: 124-125 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 3.84 (3H, s, CH3O), 4.21 (2H, s, CH2), 6.84 (2H, t, J=8.68 Hz, ArH), 7.06 (2H, t, J=8.68 Hz, ArH), 7.23˜7.26 (3H, m, ArH), 7.32˜7.36 (2H, m, ArH), 7.47 (2H, t, J=8.68 Hz, ArH), 8.08 (2H, t, J=8.96 Hz, ArH), 12.45 (1H, br, CONH); EI-MS m/e (%): 416.2 (M+, 62), 282.1 (4), 135.1 (100); HREI-MS Calcd. for C24H20N2O3S: 416.1195. found: 416.1194.

Workup

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

Sources & evidence

ORD record
ord-f49ac1e59d30439c801055b5c217918c
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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