Water → 3-(5-Bromo-benzothiazol-2-ylmethoxy)-2,6-difluoro-benzamide

HRID 415589Notes

Reaction equation

HRID 415589 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10]Br)=[N:7][C:6]=2[CH:12]=1.[F:13][C:14]1[C:22]([OH:23])=[CH:21][CH:20]=[C:19]([F:24])[C:15]=1[C:16]([NH2:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][O:23][C:22]3[C:14]([F:13])=[C:15]([C:19]([F:24])=[CH:20][CH:21]=3)[C:16]([NH2:18])=[O:17])=[N:7][C:6]=2[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 144586425-Bromo-2-(bromomethyl)-1,3-benzothiazoleHCID 451201362,6-Difluoro-3-hydroxybenzamide

Product 1

HCID 462370143-(5-Bromo-benzothiazol-2-ylmethoxy)-2,6-difluoro-benzamideYield 769.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-bromo-2-bromomethyl-benzothiazole (1.1 g, 0.358 mmol) in 5 ml of anhydrous DMF was added 2,6-difluoro-3-hydroxybenzamide (0.620 g, 0.22 mol) and potassium carbonate (1.73 g, 1.25 mmol). The reaction mixture was stirred at 25° C. for 24 h under nitrogen atmosphere. Water was added to the reaction mixture the compound was precipitated out, filtered and washed with diethylether to give the title compound as yellow solid (1.1 g, 76%). 1H NMR (DMSO-d6, 400 MHz): δ 5.71 (s, 2H), 7.11 (dt, 1H J=8.8 Hz (o-coupling), 7.38-7.39 (m, 1H), 7.65 (d, 1H, J=8.8 Hz (o-coupling), 7.90 (broad s, 1H), 8.13 (d, 1H, J=8.8 Hz (o-coupling), 8.18 (s, 1H), 8.26 (broad s, 1H). MS ES+ (400.9), HPLC (method 5) Rt=16.57 min.

Workup

  1. customwas precipitated out
  2. filtrationfiltered
  3. washwashed with diethylether

Sources & evidence

ORD record
ord-1c243904f1e14c3b88de84b25dda7c61
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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