Triethylamine → 1-[(E)-3-(3-Chloro-phenyl)-acryloyl]-[1,4]diazepan-5-one

HRID 2095484Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.[NH:19]1[CH2:25][CH2:24][C:23](=[O:26])[NH:22][CH2:21][CH2:20]1.C(N(CC)CC)C>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:5]=[CH:6]/[C:7]([N:19]2[CH2:25][CH2:24][C:23](=[O:26])[NH:22][CH2:21][CH2:20]2)=[O:9])[CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 20.00 g (109.52 mmol) of (E)-3-chlorocinnamic acid in 500 ml of dichloromethane was treated at RT with 6 drops of DMF. 10.08 ml (115.00 mmol) of oxalyl chloride in 60 ml dichloromethane were added dropwise and stirring was continued for 3 h30. The solution was evaporated, redissolved in 400 ml of dichloromethane, cooled (0° C.) and treated with a solution of 12.50 g (109.52 mmol) of [1,4]diazepan-5-one and 30.49 ml (219.05 mmol) of triethylamine in 190 ml of dichloromethane. The reaction was warmed up over night to RT and then evaporated. The precipitate was suspended in 90 ml of water, stirred 30 min, and filtered, washed with water to give, after drying under reduced pressure overnight, 28.03 g (92%) of the titled compound as a off-white powder. MS: 278.9 (MH+, 1Cl).

Workup

customThe solution was evaporated
dissolutionredissolved in 400 ml of dichloromethane
temperatureThe reaction was warmed up over night to RT
customevaporated
stirringstirred 30 min
filtrationfiltered
washwashed with water
customto give
dry with materialafter drying under reduced pressure overnight, 28.03 g (92%) of the titled compound as a off-white powder

Sources & evidence

ORD record: ord-e9dc6a81560847c9a067bc02e152a057
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445674B2

Reaction notes

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