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

HRID 370923Notes

Reaction equation

HRID 370923 reaction equation
[CH:1]([N:4]=[C:5](Cl)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)([CH3:3])[CH3:2].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].[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:5](=[N:4][CH:1]([CH3:3])[CH3:2])[C:24]2[N:20]([CH3:19])[C:21]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:22][C:23]=2[CH3:25])=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 24247Perchloric AcidHCID 24638Chlorosulfonic acidHCID 12582456N-Isopropyl 4-Chlorobenzimidoyl ChlorideHCID 13221886Methyl 1,4-dimethyl-1H-pyrrole-2-acetate

Product 1

HCID 20275545Methyl 5-[(4-chlorophenyl)(isopropylimino)methyl]-1,4-dimethyl-1H-pyrrole-2-acetate Perchlorate

Procedure

The title compound was prepared as in Example X from N-isopropyl 4-chlorobenzimidoyl chloride (10.75 g, 49.8 mmole), chlorosulfonic acid (0.58 g, 5.0 mmole), methyl 1,4-dimethyl-1H-pyrrole-2-acetate (8.34 g, 50 mmole), and 70% perchloric acid (7.8 g, 55 mmole) to yield 14.2 g (64%) of a bright yellow solid, m.p. 94°-110° C. (dec).

Sources & evidence

ORD record
ord-943a744df7234869a290f5ee810c156f
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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