1,1'-Carbonyldiimidazole → HCID 22922551, compound

HRID 1081458Notes

Reaction equation

HRID 1081458 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>C(#N)C>[CH2:16]([N:13]1[CH2:12][CH2:11][CH:10]([N:9]2[C:3]3[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=3[NH:1][C:23]2=[O:24])[CH2:15][CH2:14]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 22922520HCID 22922520, compound

Product 1

HCID 22922551HCID 22922551, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 12.71 g of the compound obtained in step B) and 8.9 g of 1,1'-carbonyldiimidazole in 130 ml of acetonitrile is refluxed for 3 hours. The solvent is evaporated off under vacuum, the residue is taken up with water, extracted with DCM, washed with a saturated solution of NaHCO3 and with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/MeOH mixture (92/8; v/v) as the eluent. 8.9 g of the expected product are obtained after recrystallization from absolute ethanol. M.p.=204°-206° C.

Workup

  1. temperatureis refluxed for 3 hours
  2. customThe solvent is evaporated off under vacuum
  3. extractionextracted with DCM
  4. washwashed with a saturated solution of NaHCO3 and with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica using a DCM/MeOH mixture (92/8; v/v) as the eluent

Sources & evidence

ORD record
ord-96cf4e7c4d0545e1b6171fda2ecd44c8
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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