Water → HCID 136376636, compound

HRID 1671334Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:12][CH3:13])=[N:8][NH:9][C:10]=1[OH:11])=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH:21]([CH3:32])[C:22]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[Cl:31])=[O:23].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:12][CH3:13])=[N:8][NH:9][C:10]=1[O:11][CH:21]([CH3:32])[C:22]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[Cl:31])=[O:23])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 3-ethyl-5-hydroxy-1H-pyrazole-4-carboxylic acid ethyl ester (1.5 g, 8.14 mmol) in DMF (10 ml) is added K2CO3 (1.15 g, 8.14 mmol). The mixture is heated to 50° C. and treated with a solution of 2-bromo-1-(2,4-dichloro-phenyl)-propan-1-one (Intermediate AA) (2.53 g, 8.96 mmol) in DMF (10 ml). Stirring continues at 50° C. for 1 hour and after cooling to RT, the reaction mixture is poured into water (300 ml, pre-cooled to 10-15° C.) which is subsequently allowed to reach ambient temperature over 3 h (with stirring). The resulting suspension is filtered, washed with water and the solid dried in vacuo overnight. The resultant crude product is triturated in diethyl ether (approx. 15 ml) for 20 mins. then dried in vacuo to yield 5-[2-(2,4-dichloro-phenyl)-1-methyl-2-oxo-ethoxy]-3-ethyl-1H-pyrazole-4-carboxylic acid ethyl ester: yield: MS: m/z 385.13 [M+H]+

Workup

temperatureafter cooling to RT
waitto reach ambient temperature over 3 h
stirring(with stirring)
filtrationThe resulting suspension is filtered
washwashed with water
customthe solid dried in vacuo overnight
customThe resultant crude product is triturated in diethyl ether (approx. 15 ml) for 20 mins
customthen dried in vacuo

Sources & evidence

ORD record: ord-e76f9075eda647baa577fad4ce605f37
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994203B2

Reaction notes

Loading…