Methanesulfonic Acid → HCID 178442894, compound

HRID 848797Notes

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:10]2=[O:32])=[CH:5][C:3]=1[NH2:4].C(O[C:36]1[CH2:40][C:39](=[O:41])[N:38]([C:42]2[C:47]([Cl:48])=[CH:46][C:45]([Cl:49])=[CH:44][C:43]=2[Cl:50])[N:37]=1)C.CS(O)(=O)=O>C(OCC)(=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:10]2=[O:32])=[CH:5][C:3]=1[NH:4][C:36]1[CH2:40][C:39](=[O:41])[N:38]([C:42]2[C:47]([Cl:48])=[CH:46][C:45]([Cl:49])=[CH:44][C:43]=2[Cl:50])[N:37]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 13.9 g of 2-chloro-5-(3-octadecylimidazolidin-2-on-1-yl)aniline, 9.3 g of 3-ethoxy-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-one and 1 g of methanesulfonic acid was heated at 150° C. under reduced pressure with stirring for 6 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 benzene as a spreading agent) to obtain the desired compound. By recrystallization from a solvent mixture of ethyl acetate and acetonitrile 10.5 g of the crystals having a melting point of 163° to 168° 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 benzene as a spreading agent)

Sources & evidence

ORD record: ord-19fe796c95394c488fc8b29dc9a83c6b
Source dataset: uspto-grants-1981_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04297440

Reaction notes

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