Acetic Acid → HCID 23048269, compound

HRID 580247Notes

Reaction equation

HRID 580247 reaction equation
[NH2:1](=S)[NH2:2].[C:4]([OH:7])(=O)[CH3:5].[C:8]1(C)[CH:13]=[CH:12]C=[CH:10][CH:9]=1>C1(C)C(C)=CC=CC=1>[NH:1]1[C:10]2[CH:5]([CH2:12][CH2:13][CH2:8][CH:9]=2)[C:4](=[O:7])[NH:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1140TolueneHCID 129772811HCID 129772811, compound

Product 1

HCID 23048269HCID 23048269, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The aminosulfide (IV) is then reacted with concentrated hydrochloric acid at a temperature of 0° to 40° C., followed by reacting the resultant hydrochloride with 1.0 to 1.5 equivalents of sodium nitrite at -10° to 5° C. to form the diazonium salt. The diazonium salt is reduced with 3.0 to 10 equivalents (in regard to the aminosulfide (IV)) of stannous chloride at 0° to -40° C. to obtain the hydrazine hydrochloride, which is neutralized with an aqueous alkaline solution (e.g. sodium hydroxide, potassium hydroxide, potassium carbonate) to obtain the hydrazine sulfide (V). The thus obtained hydrazine sulfide (V) is reacted with 1.0 to 1.2 equivalents of 2-alkoxycarbonylcyclohexanone in a solvent (e.g. acetic acid, toluene, xylene) at a temperature of 50° to 200° C. (preferably 80° to 150° C.) optionally while dehydration by azeotropic distillation or in the presence of molecular sieve is conducted to give the hexahydroindazol-3-one (II).

Workup

  1. distillationby azeotropic distillation

Sources & evidence

ORD record
ord-4ca7f12345c64887b30090ace301af26
Source dataset
uspto-grants-1988_06
Patent number
US04752325

Reaction notes

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