Iodine → HCID 14028889, compound

HRID 986084Notes

Reaction equation

HRID 986084 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.[CH2:15]([O:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)[CH3:16].II>CO>[C:18]([C:19]1[CH:20]=[CH:21][C:22]([N:25]=[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:23][CH:24]=1)([O:17][CH2:15][CH3:16])=[O:26]

Participants

5

Reactant 3

HCID 807IodineHCID 2337BenzocaineHCID 7108Phenothiazine

Product 1

HCID 14028889HCID 14028889, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a warm and stirred suspension of 4 g (0.02 mole) finely powdered phenothiazine and 4 g (0.024 mole) ethyl-p-aminobenzoate in 200 ml methanol was added a solution of 10 g of iodine in 150 ml methanol. After stirring at room temperature for 2 hours, the dark precipitate was filtered, washed repeatedly with methanol, and dissoved in 100 ml chloroform and 10 ml triethylamine. The chloroform solution was shaken with water and separated. Purification through alumina and recrystallisation from ether gave purple leaflets. Yield 5.5 g (76%).

Workup

  1. temperatureTo a warm
  2. stirringAfter stirring at room temperature for 2 hours
  3. filtrationthe dark precipitate was filtered
  4. washwashed repeatedly with methanol
  5. stirringThe chloroform solution was shaken with water
  6. customseparated
  7. customPurification
  8. customthrough alumina and recrystallisation from ether
  9. customgave purple leaflets

Sources & evidence

ORD record
ord-b23212027dd64302971d4faee6311bac
Source dataset
uspto-grants-1987_12
Patent number
US04710570

Reaction notes

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