Chloroform → HCID 12223711, compound

HRID 1658057Notes

Reaction equation

HRID 1658057 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:16]=[C:15]2[C:6]([S:7][C:8]3[CH:9]=[CH:10][CH:11]=[C:12]([C:17](O)=[O:18])[C:13]=3[NH:14]2)=[CH:5][CH:4]=1.C(Cl)(Cl)[Cl:23].P(Cl)(Cl)Cl>CN(C)C=O>[F:1][C:2]([F:21])([F:20])[C:3]1[CH:16]=[C:15]2[C:6]([S:7][C:8]3[CH:9]=[CH:10][CH:11]=[C:12]([C:17]([Cl:23])=[O:18])[C:13]=3[NH:14]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 23647FlutiazinHCID 24387Phosphorus trichloride

Product 1

HCID 12223711HCID 12223711, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Trifluoromethylphenothiazine-1-carboxylic acid (62.2 g., 0.20 mol.) was added to a stirred mixture of 300 ml. of chloroform and 300 ml. of phosphorus trichloride. The resulting brown suspension was cooled in an ice-bath while 50 ml. of dimethylformamide was added slowly until a reddish brown solution formed. After stirring the mixture for 4 hours at 25°, the chloroform and excess phosphorus trichloride were evaporated under reduced pressure. The resulting reddish brown solid residue was dissolved in 1500 ml. of boiling n-hexane. The hot, clear, reddish solution was decanted from a viscous, insoluble material and, on cooling, large red needles formed. The solid was collected by filtration and washed with hexane to give 8-trifluoromethylphenothiazine-1-carboxylic acid chloride, m.p. 124°-126°.

Workup

  1. temperatureThe resulting brown suspension was cooled in an ice-bath while 50 ml
  2. customformed
  3. customthe chloroform and excess phosphorus trichloride were evaporated under reduced pressure
  4. dissolutionThe resulting reddish brown solid residue was dissolved in 1500 ml
  5. customThe hot, clear, reddish solution was decanted from a viscous, insoluble material
  6. temperatureon cooling
  7. customlarge red needles formed
  8. filtrationThe solid was collected by filtration
  9. washwashed with hexane

Sources & evidence

ORD record
ord-516d230704054dec93bc61421a63a35b
Source dataset
uspto-grants-1976_06
Patent number
US03962438

Reaction notes

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