Boron tribromide → HCID 57991650, compound

HRID 556104Notes

Reaction equation

[CH2:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:24])[C:12]2[CH:17]=[C:16]([O:18]C)[C:15]([O:20]C)=[C:14]([O:22]C)[CH:13]=2)=[N:7][C:6]=1[C:25]1[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=1)[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br>>[CH2:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:24])[C:12]2[CH:17]=[C:16]([OH:18])[C:15]([OH:20])=[C:14]([OH:22])[CH:13]=2)=[N:7][C:6]=1[C:25]1[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 57991583HCID 57991583, compound

Product 1

HCID 57991650HCID 57991650, compoundYield 47.5%

Procedure

A procedure similar to that in Example 7 was used. N-[5-n-butyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamide prepared in Example 64 and boron tribromide were used as starting materials, the crude product was purified by recrystallization with acetone to give a product as a white solid in a yield of 47.5%, mp: 119-120 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 0.88 (3H, t, J=7.2 Hz, CH3), 1.35 (2H, sextuple, J=7.20 Hz, CH2), 1.63 (2H, quintuple, J=7.20 Hz, CH2), 2.82 (2H, t, J=7.2 Hz, CH3), 6.83 (2H, d, J=8.80 Hz, ArH), 7.08 (2H, s, ArH), 7.40 (2H, d, J=8.80 Hz, ArH), 8.80 (4H, br, OH), 12.12 (1H, br, CONH); EI-MS m/e (%): 400.1 (M+, 14), 248.2 (55), 205.1 (100), 163.1 (38); HREI-MS Calcd. for C20H20N2O5S: 400.1093. found: 400.1091.

Workup

customthe crude product was purified by recrystallization with acetone

Sources & evidence

ORD record: ord-831a86e6c75a4bbd8b1a6b78cea977c9
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053581B2

Reaction notes

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