Dimethyl Sulfoxide → HCID 54125058, compound

HRID 1587732Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([N:9]=[CH:10][N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[N:16][N+:17]([O-:19])=[O:18])[CH:5]=[CH:6][C:7]=1[CH3:8].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]Cl)=[CH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C(OCC)(=O)C.O>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:13]2[CH2:14][CH2:15][N:11]([CH:10]=[N:9][C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=3)[C:12]2=[N:16][N+:17]([O-:19])=[O:18])=[CH:23][N:22]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 71,0 g of 1-(3,4-dimethylphenyliminomethyl)-2-nitroiminoimidazolidine, 48.5 g of 2-chloro-5-chloromethylpyridine, 50.0 g of potassium carbonate and 200 g of dimethylsulfoxide was agitated at 70° C. for 1 hour. After cooling to room temperature, about 800 ml of water and about 200 ml of ethyl acetate were added to the reaction mixture, followed by agitation, separation into settled crystals and a filtrate, washing with water, drying and recrystallization of a combination of the crystals with those obtained by concentration to about 1/5 from about 400 ml of acetonitrile to give 41 g of 1-(2-chloropyridine-5-ylmethyl)-2-nitroimino-3-(3,4-dimethylphenyliminomethyl)imidazolidine.

Workup

temperatureAfter cooling to room temperature
customfollowed by agitation, separation into settled crystals
washa filtrate, washing with water
customdrying
customrecrystallization of a combination of the crystals with
customthose obtained by concentration to about 1/5 from about 400 ml of acetonitrile

Sources & evidence

ORD record: ord-fa8072b2b8d04f868b411d7584c0fc91
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05219868

Reaction notes

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