p-Toluenesulfonic acid → HCID 21424941, compound

HRID 258877Notes

Reaction equation

HRID 258877 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][N:13]([CH3:34])[CH2:14][CH2:15][CH2:16][C:17]1(O)[C:23]2[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=2[S:21][C:20]2[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=2[CH2:18]1>CC1C=CC=CC=1C>[CH3:12][N:13]([CH2:14][C:15]#[C:16][C:17]1[C:23]2[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=2[S:21][C:20]2[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=2[CH:18]=1)[CH3:34]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 21424985HCID 21424985, compound

Product 1

HCID 21424941HCID 21424941, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

63 G. of p-toluenesulfonic acid and 1,800 ml. of o-xylene are heated to boiling and the water present is distilled. The solution is reacted with 90 g. of 10-[3-(dimethylamino)-1-propyl]-8-chloro-10,11-dihydro-dibenzo[b,f]thiepin-10-ol. The reaction mixture is maintained at the boiling temperature for 45 minutes, whereby the remaining water is distilled. The mixture is cooled and poured into 90 ml. of 2N aqueous sodium hydroxide. The aqueous phase is extracted with ether. The resulting organic phase is washed three times with water and subsequently extracted three times with aqueous methanesulfonic acid. The aqueous phase is washed with water and made alkaline with concentrated sodium hydroxide. The reaction mixture is then extracted with ether, and the ether extract washed with water, dried and evaporated, whereby there is obtained N,N-dimethyl-3-(8-chloro-dibenzo[b,f]thiepin-10-yl)-2-propynylamine, which after recrystallization from hexane, has a melting point of 118°-120°. The maleate is precipitated from ethanol and melts at 178°-180°.

Workup

  1. distillationthe water present is distilled
  2. customThe solution is reacted with 90 g
  3. temperatureThe reaction mixture is maintained at the boiling temperature for 45 minutes
  4. distillationwhereby the remaining water is distilled
  5. temperatureThe mixture is cooled
  6. additionpoured into 90 ml
  7. extractionThe aqueous phase is extracted with ether
  8. washThe resulting organic phase is washed three times with water
  9. extractionsubsequently extracted three times with aqueous methanesulfonic acid
  10. washThe aqueous phase is washed with water
  11. extractionThe reaction mixture is then extracted with ether
  12. extractionthe ether extract
  13. washwashed with water
  14. customdried
  15. customevaporated

Sources & evidence

ORD record
ord-000293e3b6f14b69beea3d9bde2ebdce
Source dataset
uspto-grants-1977_07
Patent number
US04035386

Reaction notes

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