Triethylamine → 3-[3,4-Bis(acetyloxy)benzoyl]-2-oxo-1-imidazolidinecarboxamide

HRID 2292328Notes

Reaction equation

Cl.N[N:3]1[CH2:7][CH2:6][N:5]([C:8]([NH2:10])=[O:9])[C:4]1=[O:11].C(N(CC)CC)C.[C:19]([O:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[O:32][C:33](=[O:35])[CH3:34])[C:26](Cl)=[O:27])(=[O:21])[CH3:20]>ClCCl>[C:19]([O:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[O:32][C:33](=[O:35])[CH3:34])[C:26]([N:3]1[CH2:7][CH2:6][N:5]([C:8]([NH2:10])=[O:9])[C:4]1=[O:11])=[O:27])(=[O:21])[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

3-Amino-2-oxo-1-imidazolidinecarboxamide, monohydrochloride (12 g 0.006 mol) was suspended in 300 ml of dichloromethane. The suspension was cooled to 0° C. and 29.2 ml of triethylamine (0.198 mol) was added; the mixture was stirred for another 20 minutes. [3,4-Bis(acetyloxy)benzoyl]chloride (10.5 g) dissolved in 200 ml of dichloromethane was added dropwise with stirring at 0° C. and the mixture was stirred overnight at room temperature, filtered and treated with 50 ml of water. After stirring for 5 minutes, 3-[3,4-bis(acetyloxy)benzoyl]-2-oxo-1-imidazolidinecarboxamide crystallized out (7.2 g) contaminated with some triethylamine hydrochloride. The impurity was removed by treatment with water to yield 6.6 g of 3-[3,4-bis(acetyloxy)benzoyl]-2-oxo-1-imidazolidinecarboxamide, melting point 222°-224° C.

Workup

additionwas added dropwise
stirringwith stirring at 0° C.
stirringthe mixture was stirred overnight at room temperature
filtrationfiltered
additiontreated with 50 ml of water
stirringAfter stirring for 5 minutes
custom3-[3,4-bis(acetyloxy)benzoyl]-2-oxo-1-imidazolidinecarboxamide crystallized out (7.2 g)
customThe impurity was removed by treatment with water

Sources & evidence

ORD record: ord-1eb977fc06264829a978e9537a5daabf
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04801705

Reaction notes

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