Boron tribromide → HCID 57991622, compound

HRID 556103Notes

Reaction equation

[CH2:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([O:20]C)[CH:13]=2)=[N:7][C:6]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][CH:24]=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:22])[C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([OH:20])[CH:13]=2)=[N:7][C:6]=1[C:23]1[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 57991648HCID 57991648, compound

Product 1

HCID 57991622HCID 57991622, compoundYield 43.6%

Procedure

A procedure similar to that in Example 7 was used. N-[5-n-butyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4-dimethoxy-benzamide prepared in Example 63 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 43.6%, mp: 189-190 └. 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), 1.62 (2H, quintuple, J=7.20 Hz, CH2), 2.82 (2H, t, J=7.2 Hz, CH3), 6.07 (3H, br, OH), 7.65˜7.85 (3H, m, ArH), 7.32˜7.52 (4H, m, ArH), 12.12 (1H, br, CONH); EI-MS m/e (%): 384.1 (M+, 37), 248.2 (83), 205.1 (100); HREI-MS Calcd. for C20H20N2O4S: 384.1144. found: 384.1146.

Workup

customthe crude product was purified by recrystallization with acetone

Sources & evidence

ORD record: ord-1d1150e6b1904cb786e1e0e4a46ef653
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053581B2

Reaction notes

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