Ethyl chloroformate → 2-[(2-Methyl-4-(ethoxycarbonylamino)phenyl)-amino]-1-pyrroline, hydrochloride

HRID 484796Notes

Reaction equation

HRID 484796 reaction equation
[Cl:1][C:2]([O:4][CH2:5][CH3:6])=[O:3].Cl.Cl.[CH3:9][C:10]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:11]=1[NH:17][C:18]1[CH2:22][CH2:21][CH2:20][N:19]=1>>[ClH:1].[CH3:9][C:10]1[CH:15]=[C:14]([NH:16][C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH:13]=[CH:12][C:11]=1[NH:17][C:18]1[CH2:22][CH2:21][CH2:20][N:19]=1

Participants

3

Reactant 2

HCID 10928Ethyl chloroformate2×HCID 1317142942-[(2-Methyl-4-aminophenyl)amino]-1-pyrroline, dihydrochloride

Product 1

HCID 704652602-[(2-Methyl-4-(ethoxycarbonylamino)phenyl)-amino]-1-pyrroline, hydrochloride

Procedure

The title compound was prepared by the method of Example 21 using 30.5 mmole of ethyl chloroformate and 1.0 g (3.8 mmole) of the product compound of Example 9. Complete reaction, as indicated by thin-layer chromatography (See Example 21), required heating for a second day with an additional 30.5 mmole of ethyl chloroformate. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Workup

  1. customComplete reaction

Sources & evidence

ORD record
ord-831065f8e028458aacbeafbed27db1d6
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Reaction notes

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