Boron tribromide → N-[5-benzyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4,5-trihydroxy-benzamide

HRID 556072Notes

Reaction equation

HRID 556072 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:27])[C:15]2[CH:20]=[C:19]([O:21]C)[C:18]([O:23]C)=[C:17]([O:25]C)[CH:16]=2)=[N:10][C:9]=1[C:28]1[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:27])[C:15]2[CH:20]=[C:19]([OH:21])[C:18]([OH:23])=[C:17]([OH:25])[CH:16]=2)=[N:10][C:9]=1[C:28]1[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 57991634N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamide

Product 1

HCID 57991610N-[5-benzyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4,5-trihydroxy-benzamideYield 61.3%

Procedure

A procedure similar to that in Example 7 was used. N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamide prepared in Example 37 and boron tribromide were used as starting materials. The obtained crude product was recrystallized with acetone to give a product as a pale yellow solid in a yield of 61.3%, mp: 245-246 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.19 (2H, s, CH2), 6.83 (2H, d, J=8.68 Hz, ArH), 7.06 (2H, s, ArH), 7.22˜7.35 (5H, m, ArH), 7.46 (2H, d, J=8.68 Hz, ArH), 12.15 (1H, br, CONH); EI-MS m/e (%): 434.1 (M+, 6), 282.1 (100); HREI-MS Calcd. for C23H18N2O5S: 434.0936. found: 434.0936.

Workup

  1. customThe obtained crude product
  2. customwas recrystallized with acetone

Sources & evidence

ORD record
ord-96ee06c4d5924ae583a0fe71d430fc76
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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