Hydrochloric Acid → HCID 67229850, compound

HRID 1851077Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH:11]=[C:10]([CH3:14])[NH:9]2)=[CH:4][CH:3]=1.[OH-].[Ca+2].[OH-].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].Cl>O1CCOCC1>[CH2:22]([O:21][C:19]([C:11]1[C:12](=[O:13])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[NH:9][C:10]=1[CH3:14])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-(4-Fluorophenyl)-5-methyl-1H-pyrazol-3(2H)-one (20.3 g, 0.105 mol) and calcium hydroxide (17.2 g, 0.232 mol) were suspended in anhydrous 1,4-dioxane (200 mL). The resulting suspension was heated at 50° C. for 20 minutes. The heated suspension was cooled to 10° C. and a solution of benzyl chloroformate (14.9 mL, 0.105 mol) in dioxane (10 mL) was added. The resulting reaction mixture was heated at 90° C. for 3 hours. Upon completion of the reaction, the reaction mixture was slowly cooled to 0° C. After adding 1 M hydrochloric acid, the mixture was stirred at room temperature overnight. Then, the produced solid was collected by filtration, washed with cold ethanol and ether, and dried in vacuum to give the target compound (22.88 g, 66% yield).

Workup

temperatureThe heated suspension was cooled to 10° C.
customThe resulting reaction mixture
temperaturewas heated at 90° C. for 3 hours
customUpon completion of the reaction
temperaturethe reaction mixture was slowly cooled to 0° C
filtrationThen, the produced solid was collected by filtration
washwashed with cold ethanol and ether
customdried in vacuum

Sources & evidence

ORD record: ord-5faa5a7a87bb4f4fb88bae2e4bb8890e
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957102B2

Reaction notes

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