Water → HCID 178520857, compound

HRID 1061557Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[NH:8][C:4]=2[CH:3]=1.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH2:21]>COCCOCCOC>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[C:9]([C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:21])[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:19])[NH:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

5-Chloro-2-methylbenzimidazole (833 mg) was dissolved in Diglyme (4 ml), and TEA (2.43 ml) was added thereto. Benzoyl chloride (2.0 ml) was further added thereto, followed by 15 minutes of stirring at about 100° C. Water (0.1 ml) was added dropwise to the reaction solution and the whole was heated under stirring at 175° C. for 10 minutes. After the reaction solution was cooled with air, water (15 ml) was added and the mixture was stirred, then the supernatant was decanted. Methanol (5 ml) was added to the residue and the precipitated crystals were collected by filtration, washed with cold methanol, and dried to obtain 2-(5-chloro-1,3-dihydro-2H-benzimidazol-2-yliden)-1,3-diphenylpropan-1,3-dione (706 mg, 38%) as pale yellow powdery crystals. Hereinafter, the compounds of Examples 2 to 25, 119 and 126 were obtained similarly.

Workup

temperaturethe whole was heated
stirringunder stirring at 175° C. for 10 minutes
additionwas added
stirringthe mixture was stirred
customthe supernatant was decanted
additionMethanol (5 ml) was added to the residue
filtrationthe precipitated crystals were collected by filtration
washwashed with cold methanol
customdried

Sources & evidence

ORD record: ord-b6201ab7fa2d4bd58ef9d54aa8be7ef6
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960591B2

Reaction notes

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