Boron tribromide → HCID 57991609, compound

HRID 556063Notes

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]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[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]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:13]=1)=[O:7]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 57991585HCID 57991585, compound

Product 1

HCID 57991609HCID 57991609, compoundYield 62.8%

Procedure

A procedure similar to that in Example 7 was used. 3,4-dimethoxy-N-[5-(4-nitro-benzyl)-4-phenyl-thiazol-2-yl]-benzamide prepared in Example 29 and boron tribromide were used as starting materials. The obtained crude product was recrystallized with acetone and ethyl acetate to give a product as a white solid in a yield of 62.8%, mp: 244└(Dec.). 1H-NMR (DMSO-d6, 400 MHz) δ: 4.42 (2H, s, CH2), 6.81 (1H, d, J=8.40 Hz, ArH), 7.38 (1H, t, J=7.60 Hz, ArH), 7.44˜7.55 (6H, m, ArH), 7.64 (2H, d, J=8.44 Hz, ArH), 8.20 (2H, d, J=8.68 Hz, ArH), 9.32 (1H, br, OH), 9.81 (1H, br, OH), 12.38 (1H, br, CONH); EI-MS m/e (%): 447.1 (M+, 16), 311.1 (100); HREI-MS Calcd. for C23H17N3O5S: 447.0889. found: 447.0887.

Workup

customThe obtained crude product
customwas recrystallized with acetone and ethyl acetate

Sources & evidence

ORD record: ord-2c07988537074912ba3503b919e2b893
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053581B2

Reaction notes

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