1,1'-Carbonyldiimidazole → HCID 21494785, compound

HRID 1731102Notes

Reaction equation

HRID 1731102 reaction equation
[C:1]1(=[O:16])[N:5]([CH2:6][CH2:7][C:8]([OH:10])=O)[C:4](=[O:11])[C:3]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]12.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:29][N:30]1[C:39]([OH:47])([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[Cl:46])[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([Cl:48])[CH:37]=2)[N:32]=[CH:31]1>O1CCCC1>[Cl:48][C:36]1[CH:37]=[C:38]2[C:33](=[CH:34][CH:35]=1)[N:32]=[CH:31][N:30]([NH:29][C:8](=[O:10])[CH2:7][CH2:6][N:5]1[C:1](=[O:16])[C:2]3[C:3](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:4]1=[O:11])[C:39]2([OH:47])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[Cl:46]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 768593-Phthalimidopropionic acidHCID 20360436HCID 20360436, compound

Product 1

HCID 21494785HCID 21494785, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cold solution of β-phthalimidopropionic acid (2.41 g., 0.011 mole) in dry tetrahydrofuran (20 ml.) is added 1,1'-carbonyldiimidazole (1.94 g., 0.011 mole) under nitrogen. The ice bath is removed and the reaction stirred for 11/2 hours before the bath is replaced and 3-amino-6-chloro-3,4-dihydro-4-hydroxy-4-(o-chlorophenyl)-quinazoline (3.22 g., 0.01 mole) in tetrahydrofuran (25 ml.) is added. The reaction is stirred for 18 hours at ambient temperature before the reaction is concentrated in vacuo. The residue is mixed with water, neutralized with sodium bicarbonate and extracted with methylene chloride. The extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give N-[6-chloro-4-hydroxy-4-(o-chlorophenyl)-3(4H)-quinazolinyl]-1,3-dioxo-2-isoindolinepropionamide.

Workup

  1. customThe ice bath is removed
  2. stirringThe reaction is stirred for 18 hours at ambient temperature before the reaction
  3. concentrationis concentrated in vacuo
  4. additionThe residue is mixed with water
  5. extractionextracted with methylene chloride
  6. washThe extract is washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1da2a24d830644b784fb93f99074c882
Source dataset
uspto-grants-1976_11
Patent number
US03994940

Reaction notes

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