1,1'-Carbonyldiimidazole → HCID 22285038, compound

HRID 984850Notes

Reaction equation

HRID 984850 reaction equation
[NH2:1][C:2]1[C:3]([C:12]2[N:16]([CH3:17])[CH:15]=[N:14][CH:13]=2)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19]>ClC1C=CC=CC=1Cl>[CH3:17][N:16]1[C:12]2[C:3]3[CH:4]=[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:10]4=[CH:11][C:2]=3[NH:1][C:18](=[O:19])[C:13]=2[N:14]=[CH:15]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 22285034HCID 22285034, compound

Product 1

HCID 22285038HCID 22285038, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 5-(3-amino-2-naphthyl)-1-methylimidazole (Preparation 17) (0.48 g, 2.14 mmol) and 1,1′-carbonyldiimidazole (0.42 g, 2.57 mmol) in o-dichlorobenzene (22 mL) was heated at 180° C. for 5 hours. The suspension was cooled to RT, filtered, and dried under vacuum, affording the title compound as a light yellow solid (0.22 g, 42%). 1H NMR (DMSO): 11.57 (s, 1H), 8.71 (s, 1H), 8.15 (s, 1H), 8.10 (d, J=8.4, 1H), 7.89 (d, J=8.4, 1H), 7.84 (s, 1H), 7.53 (m, 1H), 7.46 (m, 1H), 4.30 (s, 3H). (ES m/z (M+H)+=250.08.

Workup

  1. temperatureThe suspension was cooled to RT
  2. filtrationfiltered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-a16bb618cf244f2297a39bd0fab69fcc
Source dataset
uspto-grants-2005_03
Patent number
US06869956B2

Reaction notes

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