Iodine chloride → HCID 86608005, compound

HRID 269014Notes

Reaction equation

HRID 269014 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[N:8]2[CH:9]=[N:10][CH:11]=[C:7]2[N:6]=[C:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:4]=1.C([O-])(=O)C.[Na+].[I:29]Cl>C(O)(=O)C.O>[I:29][C:11]1[N:10]=[CH:9][N:8]2[C:3]([C:2]([F:1])([F:22])[F:23])=[CH:4][C:5]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=3)=[N:6][C:7]=12

Participants

6

Reactant 3

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 86608006HCID 86608006, compound

Product 1

HCID 86608005HCID 86608005, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine (1.05 g, 3.17 mmol) in acetic acid (4 mL) was added at room temperature sodium acetate (0.29 g, 3.58 mmol) and drop wise a solution of iodine monochloride (0.53 g, 3.58 mmol) in acetic acid (4 mL). The reaction mixture was stirred at room temperature for 19 h, diluted slowly with water (100 mL), stirred at room temperature for 30 min, the precipitate was filtered off, washed with water and dried to give 8-iodo-4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine (1.45 g, 100%) as an orange solid. MS (EI) 457.0 [(M)+]; mp 141° C.

Workup

  1. stirringstirred at room temperature for 30 min
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-34d4ed1b161f47c2ab76e581691b6367
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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