Methanesulfonic Acid → HCID 178443168, compound

HRID 848796Notes

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])=[CH:5][C:3]=1[NH2:4].[Cl:15][C:16]1[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:23])[CH:19]=[C:18]([Cl:39])[C:17]=1[N:40]1[C:44](=[O:45])[CH2:43][C:42](OCC)=[N:41]1.CS(O)(=O)=O>C(OCC)(=O)C>[Cl:15][C:16]1[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:23])[CH:19]=[C:18]([Cl:39])[C:17]=1[N:40]1[C:44](=[O:45])[CH2:43][C:42]([NH:4][C:3]2[CH:5]=[C:6]([N:9]3[CH2:13][CH2:12][CH2:11][C:10]3=[O:14])[CH:7]=[CH:8][C:2]=2[Cl:1])=[N:41]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4.4 g of 2-chloro-5-(2-oxo-pyrrolidin-1-yl)aniline, 10.2 g of 1-(2,6-dichloro-4-tetradecyloxycarbonylphenyl)-3-ethoxy-2-pyrazolin-5-one and 0.5 g of methanesulfonic acid was stirred with heating at 150° C. under reduced pressure for 12 hours. After cooling, the reaction mixture was dissolved in ethyl acetate and washed three times with water. After distilling off the solvent, the residue was separated by a silica gel chromatography (using a solvent mixture of ethyl acetate and chloroform as a spreading agent) to obtain the desired compound. By recrystallization from acetonitrile 9 g of crystals having a melting point of 143° to 146° C. were obtained.

Workup

temperatureAfter cooling
washwashed three times with water
distillationAfter distilling off the solvent
customthe residue was separated by a silica gel chromatography (
additiona solvent mixture of ethyl acetate and chloroform as a spreading agent)

Sources & evidence

ORD record: ord-9a4120a7aa7345388e31354d9673a213
Source dataset: uspto-grants-1981_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04297440

Reaction notes

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