Sodium hydride → 1-[(E)-3-(3-Chloro-phenyl)-acryloyl]-4-(2,2-diethoxy-ethyl)-[1,4]diazepan-5-one

HRID 1867356Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of 5.02 g (18.00 mmol) of 1-[(E)-3-(3-chloro-phenyl)-acryloyl]-[1,4]diazepan-5-one in 140 ml of DMA was treated at RT with 0.86 g (19.80 mmol) of NaH (55% in oil) in four portions. After 1 h 3.72 ml (21.60 mmol) of 2-bromo-1,1-diethoxy-ethane were added over 30 min. The reaction was stirred over night and heated for 1 h at 75° C. The reaction was cooled and neutralized with cold aqueous saturated NaHCO3 and extracted with Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (CH2Cl2/MeOH 99:1 to 98:2) to yield 1.87 g (26%) of the title compound as a yellow viscous oil. MS: 395.4 (MH+, Cl).

Workup

temperatureThe reaction was cooled
extractionextracted with Et2O (3×)
washThe organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl
dry with materialdried over Na2SO4
customevaporated
custompurified by flash silica gel column (CH2Cl2/MeOH 99:1 to 98:2)

Sources & evidence

ORD record: ord-c1694f42fcba4041b501f39d4e6d14cf
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632829B2

Reaction notes

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