Iodine → HCID 10150159, compound

HRID 440616Notes

Reaction equation

HRID 440616 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1.II>CO>[F:23][C:22]([F:24])([F:25])[C:19]1[CH:18]=[CH:17][C:16]([N:15]=[C:3]2[CH:4]=[C:5]3[C:14](=[N:13][C:12]4[C:7]([S:6]3)=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH:1]=[CH:2]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 807IodineHCID 7108PhenothiazineHCID 99644-(Trifluoromethyl)aniline

Product 1

HCID 10150159HCID 10150159, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
45 °C

Procedure

Phenothiazine (2.0 g, 10 mmole) and 4-aminobenzotrifluoride (1.77 g, 11 mmole) were dissolved in methanol (MeOH) (100 mL) with warming to 45° C., treated with a solution of I2 (5.0 g, 19.4 mmole) in MeOH (80 mL) in one portion and allowed to stir for 3 h at 45° C. The reaction mixture was filtered and the collected solid was washed with MeOH (100 mL). The solid was dissolved in CHCl3 (60 mL) containing triethylamine (NEt3) (6 mL) then this solution was diluted with hexane (200 mL) and chilled in an ice bath for 2 h. The purple solid that separated was collected by filtration and redissolved in CHCl3 /NEt3 (10:1, v:v) (50 mL) and chromatographed on silica gel (250 g) using CHCl3 /acetone (96:4, v:v) development. The purple product band was collected and evaporated to dryness in vacuo to afford 4 (0.26 g, 7.3%) with mp=207°-8° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe collected solid was washed with MeOH (100 mL)
  3. dissolutionThe solid was dissolved in CHCl3 (60 mL)
  4. additioncontaining triethylamine (NEt3) (6 mL)
  5. additionthis solution was diluted with hexane (200 mL)
  6. temperaturechilled in an ice bath for 2 h
  7. filtrationThe purple solid that separated was collected by filtration
  8. dissolutionredissolved in CHCl3 /NEt3 (10:1, v:v) (50 mL)
  9. customchromatographed on silica gel (250 g)
  10. customThe purple product band was collected
  11. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-6428b51c7cb5490ca0e3527daf636c05
Source dataset
uspto-grants-1996_05
Patent number
US05520786

Reaction notes

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