Iodine → HCID 18982717, compound

HRID 1440184Notes

Reaction equation

HRID 1440184 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.C([O-])(=O)C.[K+].[C:21](#[N:25])[CH2:22][C:23]#[N:24].II>CO>[C:23]([C:22]([C:21]#[N:25])=[C:9]1[CH:10]=[C:11]2[C:6](=[N:5][C:4]3[C:13]([S:12]2)=[CH:14][CH:15]=[C:2]([Cl:1])[CH:3]=3)[CH:7]=[CH:8]1)#[N:24]

Participants

6

Reactant 4

HCID 807IodineHCID 70882-ChlorophenothiazineHCID 8010MalononitrileHCID 517044Potassium Acetate

Product 1

HCID 18982717HCID 18982717, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 2-chlorophenothiazine (1.0 g; 4.26 mmol) and potassium acetate (KOAc) (2.5 g) in boiling methanol (MeOH) (70 mL) was allowed to cool to 40° C. then treated with malononitrile (0.42 g; 1.5 eq). This solution was treated at once with a solution of I2 (2.16 g) in MeOH (25 mL) and allowed to stir at ambient temperature for 3.5 h. The dark green solid that separated was collected by filtration, washed with MeOH and dried in vacuo to give 4 (0.33 g, 26%). MS (70 eV) m/e (rel. intensity) 295 (100), 260 (26).

Workup

  1. filtrationThe dark green solid that separated was collected by filtration
  2. washwashed with MeOH
  3. customdried in vacuo

Sources & evidence

ORD record
ord-9203284edc734ad8ab5ab564e9c45599
Source dataset
uspto-grants-1996_03
Patent number
US05498542

Reaction notes

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