Boron tribromide → n-[5-Benzyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-2-hydroxy-benzamide

HRID 556070Notes

Reaction equation

HRID 556070 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21]C)=[N:10][C:9]=1[C:24]1[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][CH:25]=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:23])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:21])=[N:10][C:9]=1[C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 57991615N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-2-methoxy-benzamide

Product 1

HCID 57991592n-[5-Benzyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-2-hydroxy-benzamideYield 64.4%

Procedure

A procedure similar to that in Example 7 was used. N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-2-methyoxy-benzamide prepared in Example 36 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 64.4%, mp: 279-280 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.19 (2H, s, CH2), 6.85 (2H, d, J=8.40 Hz, ArH), 6.94˜7.02 (2H, m, ArH), 7.22˜7.28 (3H, m, ArH), 7.34 (2H, t, J=7.84 Hz, ArH), 7.42˜7.48 (3H, m, ArH), 7.96 (1H, d, J=7.84 Hz, ArH), 9.70 (1H, br, OH), 12.15 (1H, br, CONH); EI-MS m/e (%): 402.2 (M+, 63), 282.1 (100); HREI-MS Calcd. for C23H18N2O3S: 402.1038. found: 402.1037. Anal. Calcd. for C23H18N2O3S: C, 68.64; H, 4.51; N, 6.96. found: C, 68.45; H, 4.38; N, 6.80.

Workup

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

Sources & evidence

ORD record
ord-b5f0f54dfb61411a9ae4aadacfc55e4d
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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