Water → HCID 67215347, compound

HRID 1983115Notes

Reaction equation

[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([NH:15][NH2:16])=[O:14].N1([C:22]([C:24]2[CH:33]=[CH:32][C:27]3[NH:28][C:29](=[O:31])[NH:30][C:26]=3[CH:25]=2)=O)C=CN=C1.P(Cl)(Cl)(Cl)=O.O>ClC1C=CC=CC=1>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[O:14][C:22]([C:24]2[CH:33]=[CH:32][C:27]3[NH:28][C:29](=[O:31])[NH:30][C:26]=3[CH:25]=2)=[N:16][N:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid hydrazide (200 mg, 0.92 mmol) in chlorobenzene (2 mL) was added 5-(imidazole-1-carbonyl)-1,3-dihydro-benzoimidazol-2-one (315 mg, 1.38 mmol) and stirred for 18 h at 100° C. After cooling to ambient temperature phosphorus oxychloride (126 μL, 1.38 mmol) was added and the suspension was stirred for 4 h at 100° C. It was then cooled to ambient temperature and water (2 mL) was added, stirred for 15 min, and the resulting precipitate filtered off and washed with water (5 mL) and tert-butylmethylether (5 mL). Recrystallisation from ethanol afforded the title compound (257 mg, 78%) which was obtained as a light-grey solid. MS: m/e=360.1 [M+H]+.

Workup

additionwas added
stirringthe suspension was stirred for 4 h at 100° C
temperatureIt was then cooled to ambient temperature
stirringstirred for 15 min
filtrationthe resulting precipitate filtered off
washwashed with water (5 mL) and tert-butylmethylether (5 mL)
customRecrystallisation from ethanol

Sources & evidence

ORD record: ord-8911bb53a02f4e6fa41ff1e84cb0f4db
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541372B2

Reaction notes

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