2,6-Dichloroaniline → 1H-Imidazol-2-amine, 4,5-dihydro-N-(2,6-dichlorophenyl)-1-(2-quinolinylcarbonyl)-

HRID 2166828Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([N:13]1[CH2:17][CH2:16][NH:15][C:14]1=O)=[O:12].[Cl:19][C:20]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:21]=1[NH2:22].P(Cl)(Cl)(Cl)=O>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([N:13]1[CH2:17][CH2:16][N:15]=[C:14]1[NH:22][C:21]1[C:20]([Cl:19])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:27])=[O:12]

Participants

Reactant 3

HCID 118462,6-Dichloroaniline

HCID 24813Phosphorus oxychloride

HCID 570850601-(Quinolin-2-oyl)-imidazolin-2-one

Product 1

HCID 30619581H-Imidazol-2-amine, 4,5-dihydro-N-(2,6-dichlorophenyl)-1-(2-quinolinylcarbonyl)-

Procedure

Using the process described in Example 49, 1-(quinolin-2-oyl)-imidazolin-2-one and 2,6-dichloroaniline, in the presence of an excess of phosphorus oxychloride, give 1-(quinolin-2-oyl)-2-(2',6'-dichlorophenylamino)-2-imidazoline of melting point 196°-197.5° C.; the material is identical with the product obtained according to Example 46.

Sources & evidence

ORD record: ord-b38b147a92ee43749492925fd7504916
Source dataset: uspto-grants-1983_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04389403

Reaction notes

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