Potassium Carbonate → 3-[(6-Bromohexyl)oxy]benzenecarboxamide

HRID 415568

Reaction equation

C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=[O:12].[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br>CC#N>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:7][C:8]1[CH:9]=[C:10]([C:11]([NH2:13])=[O:12])[CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

(Method D) K2CO3 (1.38 g, 10 mmol, 1 equiv.) was added to a suspension of 3-hydroxybenzamide (1.37 g, 10 mmol, 1 equiv.) in CH3CN (100 ml). The mixture stirred for 10 min at room temperature, before 1,6-dibromo-hexane (9.76 g, 40 mmol, 4 equiv.) was added. The resulting mixture was stirred at 60° C. for 16 h. After this time, the reaction was cooled to room temperature, any undissolved solids were filtered off and the filtrate evaporated under reduced pressure to dryness. The residue was taken-up in EtOAc and water. The organic phase was separated and washed consecutively with K2CO3 solution, water and brine. Dried with MgSO4 and evaporated under reduced pressure to a small volume. The precipitant solid was filtered and washed with EtOAc/pentane, to give the desired compound as a white solid (2.0 g, 67%), mp 115-117° C. HPLC-MS (method 1): m/z 300 [M]+, 302 [M+2H]+, Rt=4.08 min.

Workup

additionwas added
temperatureAfter this time, the reaction was cooled to room temperature
filtrationany undissolved solids were filtered off
customthe filtrate evaporated under reduced pressure to dryness
customThe organic phase was separated
washwashed consecutively with K2CO3 solution, water and brine
dry with materialDried with MgSO4
customevaporated under reduced pressure to a small volume
filtrationThe precipitant solid was filtered
washwashed with EtOAc/pentane

Sources & evidence

ORD record: ord-cab0fd9a957e427797afc213ab8967fb
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088791B2

Linked notes

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