2-Chlorocyclohexanone → HCID 23312424, compound

HRID 745756Notes

Reaction equation

HRID 745756 reaction equation
Cl.N[C:3]1CC[N:5]([C:8]2[S:9][C:10]3[CH2:16][CH2:15][CH2:14][CH2:13][C:11]=3[N:12]=2)[N:4]=1.C(NNC(N)=S)=[O:18].[Cl:24]C1CCCCC1=O>CN(C)C=O>[ClH:24].[CH:3]([NH:4][NH:5][C:8]1[S:9][C:10]2[CH2:16][CH2:15][CH2:14][CH2:13][C:11]=2[N:12]=1)=[O:18]

Participants

5

Reactant 3

HCID 132032-ChlorocyclohexanoneHCID 27754861-Formyl-3-thiosemicarbazideHCID 23312414HCID 23312414, compound

Product 1

HCID 23312424HCID 23312424, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2-hydrazino-4,5,6,7-tetrahydro-benzothiazole hydrochloride used above is prepared in accordance with the method of Y.Usui [CA 70,96685 (1969)] via Hantzsch synthesis, with better yields by modification of the conditions. A mixture of 20 g of formylthiosemicarbazide, 22.3 g of 2-chlorocyclohexanone and 150 ml of dimethylformamide is kept at 70°-80° C. for 3 hours. On cooling, some of the product crystallises out. The dimethylformamide is distilled off in vacuo and the residue is recrystallised from ethanol. 27.4 g of 1-formyl-2-(4,5,6,7-tetrahydro-benzothiazolyl)-hydrazine hydrochloride of melting point 171°-173° C. are obtained.

Workup

  1. customabove is prepared in accordance with the method of Y.Usui [CA 70,96685 (1969)] via Hantzsch synthesis
  2. customwith better yields by modification of the conditions
  3. temperatureOn cooling
  4. customsome of the product crystallises out
  5. distillationThe dimethylformamide is distilled off in vacuo
  6. customthe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-85e79c7c84a14e198a5d9b7ae9deefdc
Source dataset
uspto-grants-1986_07
Patent number
US04600722

Reaction notes

Loading…