Diethyl Ether → 2-[[2-Methyl-4-((1-methylethoxy)carbonylamino)-phenyl]amino]-1-pyrroline, hydrochloride

HRID 484798Notes

Reaction equation

HRID 484798 reaction equation
Cl.Cl.[CH3:3][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[CH2:16][CH2:15][CH2:14][N:13]=1.[C:17](Cl)([Cl:19])=[O:18].[CH:21]([OH:24])([CH3:23])[CH3:22].C(OCC)C>C(#N)C.C1(C)C=CC=CC=1>[ClH:19].[CH3:3][C:4]1[CH:9]=[C:8]([NH:10][C:17]([O:24][CH:21]([CH3:23])[CH3:22])=[O:18])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[CH2:16][CH2:15][CH2:14][N:13]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 3776IsopropanolHCID 6371PhosgeneHCID 1317142942-[(2-Methyl-4-aminophenyl)amino]-1-pyrroline, dihydrochloride

Product 1

HCID 704657712-[[2-Methyl-4-((1-methylethoxy)carbonylamino)-phenyl]amino]-1-pyrroline, hydrochloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To 1.2 g (4.6 mmole) of the product compound of Example 9 in 30 ml of acetonitrile was added a 10% excess of phosgene in toluene. The mixture was stirred at 20° in the absence of moisture for 16 hours, at which time a large excess (20 ml) of isopropyl alcohol was added. The reaction mixture was stirred at 20° until reaction was complete, as indicated by thin-layer chromatography on silica gel (9:1 ethanol/concentrated aqueous ammonia or 74:25:1 dichloromethane/ethanol/ammonia). The product was taken up in an eight-fold excess of diethyl ether and recovered as an oil by concentrating the extract. The title compound crystallized upon standing. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Workup

  1. additionwas added
  2. customrecovered as an oil
  3. concentrationby concentrating the extract
  4. customThe title compound crystallized

Sources & evidence

ORD record
ord-ebef28dc816c4bd5887d7d9a91daacd0
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Reaction notes

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