Cesium carbonate → HCID 19040967, compound

HRID 1683818Notes

Reaction equation

[OH:1][C:2]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:3]=1[C:4]([N:6]([CH:13]([CH3:15])[CH3:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[C:27]([C:29]1[CH:41]=[CH:40][C:32]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Br)=[CH:31][CH:30]=1)#[N:28]>CN(C)C=O>[C:27]([C:29]1[CH:41]=[CH:40][C:32]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:20][C:18]2[CH:17]=[CH:16][C:3]([C:4]([N:6]([CH:13]([CH3:15])[CH3:14])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[O:5])=[C:2]([OH:1])[CH:19]=2)=[CH:31][CH:30]=1)#[N:28]

Participants

Conditions

Temperature: 40 °C

Procedure

A stirred solution of 2,4-dihydroxy-N-(1-methylethyl)-N-phenylbenzamide (358 mg, 1.32 mmol) in 6 mL of N,N-dimethylformamide is treated with cesium carbonate (520 mg, 1.58 mmol), and 5-(4-cyanophenoxy)pentyl bromide (U.S. Pat. No. 4,451,476, 354 mg, 1.32 mmol) and stirred at 40° C. for 24 hours. The reaction is partitioned between ethyl acetate and water, dried over sodium sulfate and concentrated in vacuo to afford a yellow foam. This material is purified by chromatography on silica gel (30 g) with 30-70% ethyl acetate/hexane as the eluent to afford 4-[5-(4-cyanophenoxy)pentyloxy]-2-hydroxy-N-(1-methylethyl)-N-phenylbenzamide as colorless foam.

Workup

customThe reaction is partitioned between ethyl acetate and water
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customto afford a yellow foam
customThis material is purified by chromatography on silica gel (30 g) with 30-70% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record: ord-d28ddfde7d144d5793b942a45059cbf2
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639768

Reaction notes

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