Hydrochloric Acid → HCID 20262420, compound

HRID 325913Notes

Reaction equation

HRID 325913 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1N.C(C1CCO[C:15]1=[O:19])(=O)C.[ClH:20].P(Cl)(Cl)(Cl)=O.[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=C[CH:28]=1>O>[Cl:20][CH2:30][CH2:31][C:32]1[C:15](=[O:19])[CH:2]2[N:3]([CH2:28][C:27]=1[CH3:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:1]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 8706Benzo(d)thiazol-2-amineHCID 106012-AcetylbutyrolactoneHCID 24813Phosphorus oxychloride

Product 1

HCID 20262420HCID 20262420, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 75 parts of 2-benzothiazolamine, 76 parts of 3-acetyl-4,5-dihydro-2(3H)-furanone, 2,4 parts of a hydrochloric acid solution 12 N and 270 parts of methylbenzene was stirred and refluxed for 2 hours using a water-separator. The reaction mixture was cooled and 323 parts of phosphoryl chloride were added at a temperature between 20° and 25° C. The whole was slowly heated to 110° C. and stirring was continued for 2 hours at this temperature. The solvent was evaporated and the residue was poured onto a mixture of crushed ice and ammonium hydroxide. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (92:8 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanol and 2,2'-oxybispropane, yielding 39 parts of 3-(2-chloroethyl)-2-methyl-4H-pyrido[2,1-b]benzothiazol-4-one; mp. 144° C. (intermediate 4).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. stirringstirring
  4. customThe solvent was evaporated
  5. additionthe residue was poured onto a mixture of crushed ice and ammonium hydroxide
  6. extractionThe product was extracted with trichloromethane
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (92:8 by volume) as eluent
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated
  14. customThe residue was crystallized from a mixture of 2-propanol and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-c7e6739a5b8a4a6c8d95e79aac25647c
Source dataset
uspto-grants-1984_04
Patent number
US04443451

Reaction notes

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