Perchloric Acid → Methyl 5-[(4-chlorophenyl)(cyclohexylimino)methyl]-1,4-dimethyl-1H-pyrrole-2-acetate Perchlorate

HRID 370924Notes

Reaction equation

HRID 370924 reaction equation
[CH:1]1([N:7]=[C:8](Cl)[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClS(O)(=O)=O.[CH3:22][N:23]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]1[CH2:29][C:30]([O:32][CH3:33])=[O:31].[Cl:34]([OH:38])(=[O:37])(=[O:36])=[O:35]>>[Cl:34]([OH:38])(=[O:37])(=[O:36])=[O:35].[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:8](=[N:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:27]2[N:23]([CH3:22])[C:24]([CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:25][C:26]=2[CH3:28])=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 24247Perchloric AcidHCID 24638Chlorosulfonic acidHCID 13221886Methyl 1,4-dimethyl-1H-pyrrole-2-acetateHCID 13477600N-Cyclohexyl 4-Chlorobenzimidoyl Chloride

Product 1

HCID 20275547Methyl 5-[(4-chlorophenyl)(cyclohexylimino)methyl]-1,4-dimethyl-1H-pyrrole-2-acetate Perchlorate

Procedure

The title compound was prepared as in Example X from N-cyclohexyl 4-chlorobenzimidoyl chloride (7.4 g, 29 mmole), chlorosulfonic acid (0.34 g, 3 mmole), methyl 1,4-dimethyl-1H-pyrrole-2-acetate (4.82 g, 28.86 mmole), and 70% perchloric acid (4.6 g, 32 mmole) to yield 1.97 g (14%) of a lime green solid, m.p. 196°-202° C. (dec).

Sources & evidence

ORD record
ord-74a4b0e4d6d24d7c9b516f3ff110b962
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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