Ethanolamine → N-(2-Hydroxyethyl)-N'-[4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]urea

HRID 637506Notes

Reaction equation

HRID 637506 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)=[CH:6][CH:5]=1)=[C:2]=[O:3].[OH:17][CH2:18][CH2:19][NH2:20]>CN(C)C=O>[OH:17][CH2:18][CH2:19][NH:20][C:2](=[O:3])[NH:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 202086615-(4-Isocyanatophenyl)pyrazin-2(1H)-one

Product 1

HCID 20208660N-(2-Hydroxyethyl)-N'-[4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to Example 13b, 5-[4-(isocyanato)phenyl]-2(1H)-pyrazinone was reacted with 2-hydroxyethylamine (0.5 g) in dimethylformamide (5 ml) for 17 hours at room temperature. The mixture was purified by flash chromatography (chloroform--20% methanol/80% chloroform); the desired fractions were combined and evaporated under reduced pressure to afford a residue. This residue was washed with chloroform and dried to form the title compound; δ(DMSO-d6) 3.17 (sextet, 2H, --NHCH2), 3.47 (t, 2H, --CH2OH), 7.94, 8.06 (2d, J=1 Hz, pyrazinone H's).

Workup

  1. customThe mixture was purified by flash chromatography (chloroform--20% methanol/80% chloroform)
  2. customevaporated under reduced pressure
  3. customto afford a residue
  4. washThis residue was washed with chloroform
  5. customdried

Sources & evidence

ORD record
ord-578a027e38564bb0a8fd7dc7d0c6ca01
Source dataset
uspto-grants-1985_12
Patent number
US04556711

Reaction notes

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