2-Chlorophenothiazine → Phenothiazine-2-carbonitrile

HRID 247144Notes

Reaction equation

HRID 247144 reaction equation
Cl[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.[Cu][C:17]#[N:18]>CN1CCCC1=O>[C:17]([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)#[N:18]

Participants

4

Reactant 2

HCID 70882-ChlorophenothiazineHCID 178418546HCID 178418546, compound

Product 1

HCID 98841Phenothiazine-2-carbonitrileYield 75.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2-chlorophenothiazine (70.12 g), copper (I) cyanide (32.24 g) and N-methylpyrrolidinone (150 ml) were heated at reflux for 23 hours. The reaction mixture was then quenched with water (900 ml) and sodium cyanide (29.4 g) added. After heating the mixture to 30°-40° C. the black gummy product was extracted with ethyl acetate (3×250 ml). The combined ethyl acetate layers were then washed with water (2×300 ml); some brine being used to break an emulsion which formed durng each wash. Then, after drying the solution and subsequent rotary evaporation, a brown yellow solid product of crude 2-cyanophenothiazine (51 g) was obtained. This material was purified by heating it at reflux as a solution in ethanol with added activated charcoal. After filtering the hot solution thrugh Hyflo it was rotary evaporated to near dryness which resulted in a slurry of purified yellow product which was filtered off and dried (33.3 g).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 23 hours
  3. customThe reaction mixture was then quenched with water (900 ml) and sodium cyanide (29.4 g)
  4. additionadded
  5. temperatureAfter heating the mixture to 30°-40° C. the black gummy product
  6. extractionwas extracted with ethyl acetate (3×250 ml)
  7. washThe combined ethyl acetate layers were then washed with water (2×300 ml)
  8. customformed durng each wash
  9. customThen, after drying
  10. customthe solution and subsequent rotary evaporation

Sources & evidence

ORD record
ord-164a4e4b481c48a2a4124770900801ff
Source dataset
uspto-grants-1987_11
Patent number
US04705854

Reaction notes

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