Dimethylamine → HCID 23463951, compound

HRID 444505Notes

Reaction equation

HRID 444505 reaction equation
[CH2:1]([N:8]1[C:16]([S:17][CH2:18][CH2:19][CH2:20]N(C)C)=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=[O:31])=CC=1.CNC>N1C=CC=CC=1>[CH2:1]([N:8]1[C:16]([S:17][CH2:18][CH2:19][CH2:20][OH:31])=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 73974-Toluenesulfonyl chlorideHCID 205962Dazidamine

Product 1

HCID 23463951HCID 23463951, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The resulting oil (7.3 g--yield: 61%), which tends to decompose if distillation thereof is attempted, shows by elemental analysis and under NMR spectrum to consist of practically pure 2-benzyl-3-(3-hydroxypropylthio)-indazole. (b) To a solution of 3 g (0.01 mols) of the preceding product in 15 ml of pyridine there is added 1.9 g (0.01 mols) of p-toluenesulfonylchloride. The mixture is left for 3 hours under stirring at room temperature, is then poured into 100 ml of a water-ice mixture and the oil which separates is extracted with ethyl ether. The oil which is obtained by removing the solvent is dissolved in 20 ml of a toluene solution containing 10% (0.044 mols) of dimethylamine and the resulting solution is heated for 16 hours at 120° in a closed test tube. At the end of the heating cycle, the toluene solution is extracted with an equal volume of 2 N HCl and made basic with NaOH. The oil which separates is extracted with ether and to the ether solution there is added gaseous HCl. The hydrochloride which precipitates is removed by filtration and recrystallized from isopropanol-isopropyl ether.

Workup

  1. distillationto decompose if distillation
  2. extractionthe oil which separates is extracted with ethyl ether
  3. customThe oil which is obtained
  4. customby removing the solvent
  5. dissolutionis dissolved in 20 ml of a toluene solution
  6. temperaturethe resulting solution is heated for 16 hours at 120° in a closed test tube
  7. extractionAt the end of the heating cycle, the toluene solution is extracted with an equal volume of 2 N HCl
  8. extractionThe oil which separates is extracted with ether and to the ether solution
  9. additionthere is added gaseous HCl
  10. customThe hydrochloride which precipitates
  11. customis removed by filtration
  12. customrecrystallized from isopropanol-isopropyl ether

Sources & evidence

ORD record
ord-a0ab09f2c8b647ceac06ce1060a39ef8
Source dataset
uspto-grants-1981_04
Patent number
US04264618

Reaction notes

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