ethyl 1H-imidazole-2-carboxylate → HCID 18790686, compound

HRID 1107028Notes

Reaction equation

HRID 1107028 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([O:8][CH2:9][CH3:10])=[O:7].Br[CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[C:21]#[N:22])[C:13]1=[O:23]>ClCCl>[C:21]([C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[CH2:20][CH:12]([N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:13]2=[O:23])#[N:22]

Participants

4

Reactant 2

HCID 549404ethyl 1H-imidazole-2-carboxylateHCID 18790631HCID 18790631, compound

Product 1

HCID 18790686HCID 18790686, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

Ethyl 1-[(4-cyano-1-oxoindan-2-yl)]imidazole-2-carboxylate can be obtained in the following way: a mixture of 3.92 g of ethyl imidazole-2-carboxylate and 3.4 g of 2-bromo-4-cyano-1-indanone is heated at 130° C. for 20 minutes, cooled to 20° C. and dissolved in 20 ml of dichloromethane. The mixture is then concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 40° C. The residue thus obtained is purified by flash chromatography on a silica column, under a nitrogen stream at medium pressure (0.5 bar), with a dichloromethane/methanol (95/5 by volume) mixture as eluent. 1.5 g of ethyl 1-[(4-cyano-1-oxoindan-2-yl)]imidazole-2-carboxylate are thus obtained, which product melts at 159° C.

Workup

  1. temperaturecooled to 20° C.
  2. concentrationThe mixture is then concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 40° C
  3. customThe residue thus obtained
  4. customis purified by flash chromatography on a silica column, under a nitrogen stream at medium pressure (0.5 bar)

Sources & evidence

ORD record
ord-aa00367c802c45df9209c32908d32076
Source dataset
uspto-grants-2000_05
Patent number
US06057454

Reaction notes

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