Dichloromethane → Tienocarbine

HRID 647928Notes

Reaction equation

HRID 647928 reaction equation
Cl.[NH:2]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[C:9]([CH3:12])[C:8]=2[CH:13]=1)N.C(Cl)Cl.[CH3:17][N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1.[OH-].[Na+]>O>[CH3:12][C:9]1[C:8]2=[C:13]3[C:4](=[CH:5][CH:6]=[C:7]2[S:11][CH:10]=1)[NH:2][C:21]1[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][C:20]3=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 740491-Methyl-4-piperidoneHCID 204843225-Hydrazino-3-methylbenzothiophene hydrochloride

Product 1

HCID 71140Tienocarbine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

15,75 g of 5-hydrazino-3-methylbenzothiophene hydrochloride are suspended in 500 ml of water, a layer of methylene chloride is introduced under the suspension and 10.5 g of 1-methyl-4-piperidone are added at about 0° C. The mixture is then adjusted to pH 9.5 with N NaOH and is stirred for 30 minutes. The organic phase is separated off and washed with saturated NaCl solution, dried and mixed with 500 ml of ethylene glycol and the methylene chloride is distilled off under a vacuum of 12 mm. Some of the glycol is then distilled off under 0.01 mm and at 100° C. and the concentrated solution is heated to 200° C. (bath temperature) in an N2 atmosphere for 1/2 hour. The crystals which precipitate on cooling the mixture are filtered off, washed and recrystallised from ethyl acetate. Melting point: 224°-227° C.

Workup

  1. additionare added at about 0° C
  2. customThe organic phase is separated off
  3. washwashed with saturated NaCl solution
  4. customdried
  5. additionmixed with 500 ml of ethylene glycol
  6. distillationthe methylene chloride is distilled off under a vacuum of 12 mm
  7. distillationSome of the glycol is then distilled off under 0.01 mm and at 100° C.
  8. customThe crystals which precipitate
  9. temperatureon cooling the mixture
  10. filtrationare filtered off
  11. washwashed
  12. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-2b59b9bdaff6450eba2b60dd4df3d5a4
Source dataset
uspto-grants-1983_10
Patent number
US04410536

Reaction notes

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