Boron tribromide → 3,4-dihydroxy-N-[4-(4-hydroxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamide

HRID 556065Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[O:35]C)[C:6]([NH:8][C:9]1[S:10][C:11]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)[N:13]=1)=[O:7].B(Br)(Br)Br>>[OH:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[OH:35])[C:6]([NH:8][C:9]1[S:10][C:11]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[N:13]=1)=[O:7]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 579915963,4-dimethoxy-N-[4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamide

Product 1

HCID 866366303,4-dihydroxy-N-[4-(4-hydroxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamideYield 66.7%

Procedure

A procedure similar to that in Example 7 was used. 3,4-dimethoxy-N-[4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamide prepared in Example 28 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 66.7%, mp: 195-196 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.33 (2H, s, CH2), 6.74˜6.81 (3H, m, ArH), 7.37˜7.50 (6H, m, ArH), 8.16 (2H, d, J=8.80 Hz, ArH), 9.30 (1H, br, OH), 9.59 (1H, br, OH), 9.77 (1H, br, OH), 12.30 (1H, br, CONH); EI-MS m/e (%): 463.1 (M+, 1), 327.1 (100); HREI-MS Calcd. for C23H17N3O6S: 463.0838. found: 463.0822.

Workup

customThe obtained crude product
customwas recrystallized with acetone

Sources & evidence

ORD record: ord-47b8adc550a54c0f95e3d0edb9aa7779
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053581B2

Reaction notes

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