Boron tribromide → HCID 57991579, compound

HRID 556090Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([O:28]C)[C:25]=1[O:26]C)[C:6]([NH:8][C:9]1[S:10][C:11]([CH3:22])=[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:23]=[C:24]([OH:28])[C:25]=1[OH:26])[C:6]([NH:8][C:9]1[S:10][C:11]([CH3:22])=[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 1349290HCID 1349290, compound

Product 1

HCID 57991579HCID 57991579, compoundYield 60.5%

Procedure

A procedure similar to that in Example 7 was used. 3,4,5-trimethoxy-N-[4-(4-methoxy-phenyl)-5-methyl-thiazol-2-yl]-benzamide prepared in Example 53 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 60.5%, mp: 262-263 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 2.36 (3H, s, CH3), 6.76 (2H, d, J=8.80 Hz, ArH), 7.02 (2H, s, ArH), 7.41 (2H, d, J=8.80 Hz, ArH), 9.10 (2H, br, OH), 9.50 (1H, br, OH), 12.06 (1H, br, CONH); EI-MS m/e (%): 358.1 (M+, 25), 206.2 (100), 153.1 (20); HREI-MS Calcd. for C17H14N2O5S: 358.0623. found: 358.0621.

Workup

customThe obtained crude product
customwas recrystallized with acetone

Sources & evidence

ORD record: ord-350a3c2ee00b4385bc183013a3a064f5
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053581B2

Reaction notes

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