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

HRID 556097Notes

Reaction equation

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

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 579916143,4-dimethoxy-N-[4-(4-methoxy-phenyl)-5-phenylethyl-thiazol-2-yl]-benzamide

Product 1

HCID 579916003,4-dihydroxy-N-[4-(4-hydroxy-phenyl)-5-phenylethyl-thiazol-2-yl]-benzamideYield 53.8%

Procedure

A procedure similar to that in Example 7 was used. 3,4-dimethoxy-N-[4-(4-methoxy-phenyl)-5-phenylethyl-thiazol-2-yl]-benzamide prepared in Example 58 and boron tribromide were used as starting materials, the crude product was purified by recrystallization with ethyl acetate to obtain a product as a white solid in a yield of 53.8%, mp: 208-209 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 2.94 (2H, t, J=7.60 Hz, CH2), 3.11 (2H, t, J=7.60 Hz, CH2), 6.81 (3H, d, J=8.40 Hz, ArH), 7.17˜7.31 (5H, m, ArH), 7.35 (2H, t, J=7.60 Hz, CH2), 7.47˜7.55 (2H, m, ArH), 12.23 (1H, br, CONH); EI-MS m/e (%): 432.1 (M+, 4), 205.0 (100), 163.0 (28); HREI-MS Calcd. for C24H20N2O4S: 432.1144. found: 432.1140.

Workup

customthe crude product was purified by recrystallization with ethyl acetate

Sources & evidence

ORD record: ord-32242d34d8184ad3addc92e2556a3d53
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053581B2

Reaction notes

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