Perchloric Acid → Methyl 1,4-Dimethyl-5-[(methylimino)(4-nitrophenyl)methyl]-1H-pyrrole-2-acetate Perchlorate

HRID 370921Notes

Reaction equation

HRID 370921 reaction equation
[CH3:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.ClS(O)(=O)=O.[CH3:19][N:20]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]1[CH2:26][C:27]([O:29][CH3:30])=[O:28].[Cl:31]([OH:35])(=[O:34])(=[O:33])=[O:32]>>[Cl:31]([OH:35])(=[O:34])(=[O:33])=[O:32].[CH3:19][N:20]1[C:24]([C:3](=[N:2][CH3:1])[C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=2)=[C:23]([CH3:25])[CH:22]=[C:21]1[CH2:26][C:27]([O:29][CH3:30])=[O:28]

Participants

5

Reactant 4

HCID 24247Perchloric AcidHCID 24638Chlorosulfonic acidHCID 12410498N-Methyl 4-Nitrobenzimidoyl ChlorideHCID 13221886Methyl 1,4-dimethyl-1H-pyrrole-2-acetate

Product 1

HCID 20275543Methyl 1,4-Dimethyl-5-[(methylimino)(4-nitrophenyl)methyl]-1H-pyrrole-2-acetate Perchlorate

Procedure

The title compound was prepared as in Example X from N-methyl 4-nitrobenzimidoyl chloride (2.0 g, 10.1 mmole) in alcohol free chloroform (30 ml), chlorosulfonic acid (0.12 g, 1 mmole), methyl 1,4-dimethyl-1H-pyrrole-2-acetate (1.68 g, 10.06 mmole) and 70% perchloric acid (1.57 g, 11 mmole) to yield 2.77 g (65%) of a yellow solid, m.p. 108° C. (dec).

Sources & evidence

ORD record
ord-25f192e94eca461997ad4dab806372ee
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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