Sodium hydride → HCID 10004024, compound

HRID 247983Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][NH:31][C:32](=[O:34])[CH3:33].[H-].[Na+]>O1CCCC1>[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][N:31]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:32](=[O:34])[CH3:33]

Participants

Conditions

Temperature: 0 °C

Procedure

The title compound is prepared by the procedure of Example 27 using 2.45 g of product from Example 22, 0.960 g of product from Example 12, 0.322 g of washed 50% sodium hydride and 30 ml of tetrahydrofuran. The reaction is stirred at 0° C. for 1 hour, room temperature for 18 hours; followed by heating at reflux temperature for 6 hours. The residue is purified by column chromatography (silica gel: 80% ethyl acetate/hexane) to give 0.976 g of the desired product as a yellow oil. The spectral data shows the presence of 2 rotomers.

Workup

temperatureby heating
temperatureat reflux temperature for 6 hours
customThe residue is purified by column chromatography (silica gel: 80% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-d09ecf70b30b4f1d882d81c75e4cfcf2
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05208247

Reaction notes

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