Riluzole → 2-Hydrazinyl-6-(trifluoromethoxy)-1,3-benzothiazole

HRID 865796

Reaction equation

HRID 865796 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.O.[NH2:17]N.Cl.Cl.NN>C(O)CO>[NH:1]([C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:13])[F:14])[CH:8]=[CH:7][C:5]=2[N:6]=1)[NH2:17]

Participants

5

Reactant 3

HCID 5070RiluzoleHCID 17548Hydrazine, dihydrochlorideHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 104221582-Hydrazinyl-6-(trifluoromethoxy)-1,3-benzothiazoleYield 90.3%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
140 °C

Procedure

To a suspension of 93.6 g of 2-amino-6-trifluoromethoxybenzothiazole in 420 cm3 of ethylene glycol under a stream of nitrogen are added 48 g of hydrazine hydrate and 42 g of hydrazine dihydrochloride. The mixture is heated for 2 hours at 140° C. After cooling, the precipitate is filtered off and triturated with a water/diethyl ether mixture (1/1 by volume). 89.9 g of 2-hydrazino-6-trifluoromethoxybenzothiazole are thus obtained, melting at 208° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate is filtered off
  3. customtriturated with a water/diethyl ether mixture (1/1 by volume)

Sources & evidence

ORD record
ord-45efd324a5be422a87f5ea1d11e02b26
Source dataset
uspto-grants-1996_10
Patent number
US05567822

Linked notes

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