1,1'-Carbonyldiimidazole → HCID 20454780, compound

HRID 1576756Notes

Reaction equation

HRID 1576756 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][CH2:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:15])[CH3:2].[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18]>O1CCCC1>[CH3:14][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:8]=1[CH2:7][N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:16])[C:17](=[O:18])[NH:15]2

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 12204071HCID 12204071, compound

Product 1

HCID 20454780HCID 20454780, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of 15.00 g (67 mmole) of N-(2-amino-6-methyl benzyl) glycine ethyl ester in 300 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere was added a solution of 11.72 g (72 mmole) of 1,1'-carbonyldiimidazole in 200 ml of anhydrous tetrahydrofuran at such a rate that the temperature did not exceed 5°. Upon complete addition, the solution was allowed to stir at room temperature for 2 hrs., heated to reflux for 18 hrs., cooled to room temperature and the tetrahydrofuran removed in vacuo. The residue was dissolved in methylene chloride (250ml), washed with 5% aqueous hydrochloric acid (2 × 100 ml), then water (100 ml). The methylene chloride extract was dried (Na2SO4) and the solvent removed in vacuo affording 14.0 g (83% yield) of a colorless solid. Purification was effected by crystallization from nitromethane; mp 184°-5°.

Workup

  1. customdid not exceed 5°
  2. additionUpon complete addition
  3. temperature, heated
  4. temperatureto reflux for 18 hrs
  5. temperature, cooled to room temperature
  6. customthe tetrahydrofuran removed in vacuo
  7. dissolutionThe residue was dissolved in methylene chloride (250ml)
  8. washwashed with 5% aqueous hydrochloric acid (2 × 100 ml)
  9. extractionThe methylene chloride extract
  10. dry with materialwas dried (Na2SO4)
  11. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a46fe0a3e8824887a434e063290deba9
Source dataset
uspto-grants-1976_09
Patent number
US03983119

Reaction notes

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