Hydrazine hydrate (1:1) → HCID 20406533, compound

HRID 615821Notes

Reaction equation

HRID 615821 reaction equation
[CH2:1]([S:3]([C:6]1[S:7][C:8](S(CC)(=O)=O)=[N:9][N:10]=1)(=[O:5])=[O:4])[CH3:2].O.[NH2:17][NH2:18]>CO>[NH:17]([C:8]1[S:7][C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[N:10][N:9]=1)[NH2:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20406539HCID 20406539, compound

Product 1

HCID 20406533HCID 20406533, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,5-bis(ethanesulphonyl)-1,3,4-thiadiazole (67.5 g) was added portionwise to a stirred solution of hydrazine hydrate (25.8 g) in methanol (1000 ml) at room temperature. The mixture was then stirred for 20 minutes and filtered. The solid was crystallised from methanol to give 2-hydrazino-5-ethylsulphonyl-1,3,4-thiadiazole (16.5 g, mp 166°-167° C.). The corresponding semicarbazone was prepared from this compound by reaction with acetaldehyde, then with methylisocyanate by methods analogous to those of Example 1(c) and 1(d), and the title compound was generated by the method of Example 13, mp 151°-153° C.

Workup

  1. filtrationfiltered
  2. customThe solid was crystallised from methanol

Sources & evidence

ORD record
ord-b579676623d248beb6ce9ab84d3be80d
Source dataset
uspto-grants-1985_02
Patent number
US04501605

Reaction notes

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