Hydrochloric Acid → HCID 20262420, compound

HRID 371092Notes

Reaction equation

HRID 371092 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 12N 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 columnchromatography 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 columnchromatography 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-0d994715ad004de7962640e6c46b6933
Source dataset
uspto-grants-1985_07
Patent number
US04529727

Reaction notes

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