Thionyl Chloride → HCID 21999690, compound

HRID 1975884Notes

Reaction equation

HRID 1975884 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[N:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[C:20]=[S:21].S(Cl)([Cl:32])=O>C(Cl)(Cl)Cl>[ClH:1].[ClH:32].[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:20]3[S:21][C:23]4[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:22]=4[N:19]=3)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 752934-Methoxyphenyl isothiocyanateHCID 21999702HCID 21999702, compound

Product 1

HCID 21999690HCID 21999690, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4-(3,4-dichlorophenyl)-1-piperazinepropanamine (0.009 mol), prepared according to the procedure described in Example A.5, and 1-isothiocyanato-4-methoxy-benzene (0.009 mol) in CHCl3 (100 ml) was stirred for one hour at room temperature, then cooled to 0° C. on an ice-bath. Thionylchloride (30 ml) was added dropwise and the resulting reaction mixture was allowed to slowly warm to room temperature. The reaction mixture was stirred for 3 hours at 60° C. The mixture was cooled to room temperature and the resulting precipitate was filtered off, stirred in boiling 2-propanone, filtered off, then dried. This fraction was converted into the free base by addition of aqueous ammonia. The mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent evaporated. The residue was crystallized from CH3CN, filtered off, dissolved in 2-propanone and converted into the hydrochloric acid salt (1:2) with HCl/2-propanol. The precipitate was filtered off and dried, yielding 1.6 g (34%) of N-[3-[4-(3,4-dichlorophenyl)-1-piperazinyl]propyl]-6-methoxy-2-benzothiazolamine dihydrochloride (comp. 72).

Workup

  1. customprepared
  2. temperaturecooled to 0° C. on an ice-bath
  3. customthe resulting reaction mixture
  4. temperatureto slowly warm to room temperature
  5. stirringThe reaction mixture was stirred for 3 hours at 60° C
  6. temperatureThe mixture was cooled to room temperature
  7. filtrationthe resulting precipitate was filtered off
  8. stirringstirred
  9. filtrationfiltered off
  10. customdried
  11. additionThis fraction was converted into the free base by addition of aqueous ammonia
  12. extractionThe mixture was extracted with CH2Cl2
  13. customThe separated organic layer was dried
  14. filtrationfiltered
  15. customthe solvent evaporated
  16. customThe residue was crystallized from CH3CN
  17. filtrationfiltered off
  18. dissolutiondissolved in 2-propanone
  19. filtrationThe precipitate was filtered off
  20. customdried

Sources & evidence

ORD record
ord-db8a02457ee949909b4898cdade30408
Source dataset
uspto-grants-2001_05
Patent number
US06224849B1

Reaction notes

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