Boron tribromide → HCID 57991641, compound

HRID 556091Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][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]=[CH:24][C:25]=1[OH:26])[C:6]([NH:8][C:9]1[S:10][C:11]([CH3:22])=[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 5072926HCID 5072926, compound

Product 1

HCID 57991641HCID 57991641, compoundYield 61.2%

Procedure

A procedure similar to that in Example 7 was used. 3,4-dimethoxy-N-[4-(4-methoxy-phenyl)-5-methyl-thiazol-2-yl]-benzamide prepared in Example 54 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 61.2%, mp: 285└(Dec.). 1H-NMR (CD3OD, 400 MHz) δ: 2.46 (3H, s, ArCH3), 6.88˜6.98 (3H, m, ArH), 7.40˜7.51 (4H, m, ArH); EI-MS m/e (%): 342.1 (M+, 29), 206.2 (100), 137.1 (36); HREI-MS Calcd. for C17H14N2O4S: 342.0674. found: 342.0670.

Workup

customThe obtained crude product
customwas recrystallized with acetone

Sources & evidence

ORD record: ord-542a7ea54dce465d88c117b95e9bbbc1
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053581B2

Reaction notes

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