Imidazole → HCID 12150196, compound

HRID 1993322Notes

Reaction equation

HRID 1993322 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Cl[CH2:9][CH2:10][C:11]1[N:20]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]3[O:27][CH2:28][O:29][C:23]=3[CH:22]=2)[C:18]2[C:13](=[CH:14][C:15]3[O:32][CH2:31][O:30][C:16]=3[CH:17]=2)[N:12]=1.[Na+].[I-]>CN(C=O)C.CCCCCC>[N:3]1([CH2:9][CH2:10][C:11]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]4[O:27][CH2:28][O:29][C:23]=4[CH:22]=3)[C:18]3[C:13](=[CH:14][C:15]4[O:32][CH2:31][O:30][C:16]=4[CH:17]=3)[N:12]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 23505611HCID 23505611, compound

Product 1

HCID 12150196HCID 12150196, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a suspension of hexane washed NaH (60% in oil, 84 mg, 2.1 mmol) in dry DMF (5 mL) was added imidazole (142 mg, 2.1 mmol). The mixture was stirred at rt for 15 min and was treated with 2-chloroethyl-6,7-methylenedioxy-4-(3,4-methylenedioxyphenyl)quinazoline (232 mg, 0.7 mmol), and then with NaI (105 mg, 0.7 mmol). The mixture was stirred at rt for 15 h and it was poured into ice-water. The precipitated solid was collected by filtration, washed with water, and air dried. The yellow solid was then crystallized from EtOAc to give the title compound as pale yellow needles (101 mg); mp 160-163° C.; 1H NMR (CDCl3) 7.5 (s, 1H), 7.33 (s, 1H), 7.27 (s, 1H), 7.15-7.20 (m, 2H), 6.91-7.05 (m, 3H), 6.15 (s, 2H), 6.08 (s, 2H), 4.60 (m, 2H), 3.53 (m, 2H). Anal. calcd. for C21H16N4O4: C, 64.94; H, 4.15; N, 14.43. Found: C, 64.52; H, 4.11; N, 14.12.

Workup

  1. stirringThe mixture was stirred at rt for 15 h
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water, and air
  4. customdried
  5. customThe yellow solid was then crystallized from EtOAc

Sources & evidence

ORD record
ord-c6fa179dc553449d990b007a0c596b6f
Source dataset
uspto-grants-2010_01
Patent number
US07652006B2

Reaction notes

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