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

HRID 556084Notes

Reaction equation

HRID 556084 reaction equation
[CH:1]1([CH2:7][C:8]2[S:12][C:11]([NH:13][C:14](=[O:27])[C:15]3[CH:20]=[C:19]([O:21]C)[C:18]([O:23]C)=[C:17]([O:25]C)[CH:16]=3)=[N:10][C:9]=2[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>>[CH:1]1([CH2:7][C:8]2[S:12][C:11]([NH:13][C:14](=[O:27])[C:15]3[CH:16]=[C:17]([OH:25])[C:18]([OH:23])=[C:19]([OH:21])[CH:20]=3)=[N:10][C:9]=2[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 86636632N-[5-cyclohexylmethyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamide

Product 1

HCID 57991635N-[5-cyclohexylmethyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4,5-trihydroxy-benzamideYield 55.8%

Procedure

A procedure similar to that in Example 7 was used. N-[5-cyclohexylmethyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamide prepared in Example 50 and boron tribromide were used as starting materials. The obtained crude product was recrystallized with acetone to obtain a product as a white solid in a yield of 55.8%, mp: 238-239 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 0.80˜0.90 (2H, m), 1.00˜1.23 (3H, m), 1.45˜1.75 (6H, m), 2.70 (2H, d, J=7.00 Hz, CHCH2Ar), 6.84 (2H, d, J=8.68 Hz, ArH), 7.09 (2H, s, ArH), 7.38 (2H, d, J=8.68 Hz, ArH), 9.17 (4H, br, 4×OH), 12.20 (1H, br, CONH); EI-MS m/e (%): 440.0 (M+, 6), 288.1 (38), 205.1 (100), 163.0 (28); HREI-MS Calcd. for C23H24N2O5S: 440.1406. found: 440.1406.

Workup

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

Sources & evidence

ORD record
ord-b28eac7eb78d4c8aa6f07c36cc9cdf3b
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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