Bromine → HCID 23499174, compound

HRID 1836274Notes

Reaction equation

HRID 1836274 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[NH:12][CH2:13][CH2:14][N:15]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Br:16]Br>C(O)(=O)C>[BrH:16].[Br:16][C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][CH2:2][CH2:1]2)=[CH:5][C:6]=1[NH:10][C:11]1[NH:15][CH2:14][CH2:13][N:12]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 10198118HCID 10198118, compound

Product 1

HCID 23499174HCID 23499174, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2-(5-Indanylamino)-2-imidazoline (100 mg, 0.497 mmol) in acetic acid (7 mL) was added a solution of bromine (153 mg, 0.957 mmol) in acetic acid (1 mL). The resulting mixture was stirred for 5 min, and the solvent was removed. The residue was flash chromatographed over silica gel (EtOAc:MeOH:Et3N=6:2:1) to afford a solid, which was recrystallized from dichloromethane/hexane to give a beige solid (25 mg, 14% yield): mp 220-221° C.; HRMS (EI) calcd. for C12H14N3Br 279.0371, obsd. 279.0383. Anal. Calcd. for C12H14N3BrH·Br2/3H2O: C, 38.63; H, 4.41; N, 11.26; Br, 42.83. Found: C, 39.10; H, 4.21; N, 10.87; Br, 42.37.

Workup

  1. customthe solvent was removed
  2. customchromatographed over silica gel (EtOAc:MeOH:Et3N=6:2:1)
  3. customto afford a solid, which
  4. customwas recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-ab6df324eefe49379e57424ada11d86e
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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