Ethanol → HCID 13730769, compound

HRID 1650090Notes

Reaction equation

HRID 1650090 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].Br[C:11]1[C:12](=[O:24])[N:13]([CH:18]([CH:21]([CH3:23])[CH3:22])[C:19]#[N:20])[C:14](=[O:17])[C:15]=1C.[CH2:25](O)C>>[C:19]([C:18]([N:13]1[C:12](=[O:24])[CH:11]=[C:15]([NH:1][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH2:4][OH:5])[C:14]1=[O:17])([CH3:25])[CH:21]([CH3:22])[CH3:23])#[N:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 214392-Aminobenzyl alcoholHCID 54230747HCID 54230747, compound

Product 1

HCID 13730769HCID 13730769, compound

Procedure

To o-aminobenzyl alcohol, (2 g, 0.0125 mol) and 3-bromo- -isopropyl- -methyl-2,5-dioxo-3-pyrroline-1-acetonitrile (2.7 g, 0.01 mol) is added absolute ethanol (100 ml) containing 3 g of 5 A pulverized sieves. The mixture is stirred for 20 hours at room temperature. The solvent is removed and the residue is purified through a silica gel dry column, eluant ether-hexane (2:1). Starting bromomaleimide is first recovered, followed by a bright yellow solid 1.89 g (60%), mp 39°-45° C. Anal. calcd. for C17H19N3O3 : C, 65.16; H, 6.11; N, 13.41. Found: C, 65.94; H, 6.21; N, 12.87.

Workup

  1. customThe solvent is removed
  2. customthe residue is purified through a silica gel
  3. dry with materialdry column, eluant ether-hexane (2:1)
  4. customStarting bromomaleimide is first recovered

Sources & evidence

ORD record
ord-22a9589504b244298c665115ffa1bbd1
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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