1,1'-Carbonyldiimidazole → 7-Bromo-3,4-dihydro-2(1H)-quinazolinone

HRID 1520109Notes

Reaction equation

HRID 1520109 reaction equation
[NH2:1][CH2:2][C:3]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:4]=1[NH2:5].C1N=CN([C:16](N2C=NC=C2)=[O:17])C=1>C1COCC1>[Br:10][C:7]1[CH:6]=[C:4]2[C:3]([CH2:2][NH:1][C:16](=[O:17])[NH:5]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 223913142-(Aminomethyl)-5-bromoaniline

Product 1

HCID 468564837-Bromo-3,4-dihydro-2(1H)-quinazolinoneYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of compound 12 (0.90 g, 4.5 mmol) in THF (10 mL) at room temperature was added CDI (0.80 g, 4.95 mmol), and the reaction was stirred at 80° C. for 6 hr. The mixture was cooled to room temperature, and the solid formed was filtered, washed with diethyl ether to afford 0.73 g (72%) of compound 13 as off-white solid. IR (KBr) νmax. cm−1: 3308, 3158 (NH), 3022 (Ar—H), 1682 (C═O), 1514, 1411 (C═C). 1H NMR (500 MHz, DMSO-d6) δ=5.25 (s, 2H, CH2); 6.82 (d, 1H, J=8.2 Hz, H-5); 7.42 (m, 2H, H-4, H-6); 10.29 (br. s, 1H, NH); 13C NMR (125.7 MHz, DMSO-d6)=66.85 (CH2), 113.70 (C-10), 115.70 (C-8), 121.03 (C-7), 127.52 (C-6), 131.41 (C-5), 135.88 (C-9), 151.42 (C═O). Calculated (%) for C8H7BrN2O (225.97); C: 42.32, H: 3.11, N: 12.34. found (%); C: 42.27, H: 3.16, N: 12.28.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solid formed
  3. filtrationwas filtered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-9e77c8a1ddb4424ba7a80188223b39eb
Source dataset
uspto-grants-2015_07
Patent number
US09073900B2

Reaction notes

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