Toluene → 3-(2,4-dichloro-6-fluorobenzothiazol-7-yl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one

HRID 21732Notes

Reaction equation

HRID 21732 reaction equation
[Cl:1][C:2]1[S:3][C:4]2[C:10]([N:11]([C:13](=[O:18])C(C)(C)C)[NH2:12])=[C:9]([F:19])[CH:8]=[C:7]([Cl:20])[C:5]=2[N:6]=1.[C:21](Cl)(Cl)=[O:22].[C:25]1([CH3:31])[CH:30]=CC=C[CH:26]=1>>[Cl:1][C:2]1[S:3][C:4]2[C:10]([N:11]3[N:12]=[C:21]([C:25]([CH3:31])([CH3:30])[CH3:26])[O:22][C:13]3=[O:18])=[C:9]([F:19])[CH:8]=[C:7]([Cl:20])[C:5]=2[N:6]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 199334582,4-dichloro-6-fluoro-7-[N-(2,2-dimethylpropanoyl)hydrazino]benzothiazole

Product 1

HCID 199334683-(2,4-dichloro-6-fluorobenzothiazol-7-yl)-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one

Procedure

A solution of 1,4 g 2,4-dichloro-6-fluoro-7-[N-(2,2-dimethylpropanoyl)hydrazino]benzothiazole in 8 ml of a 20% solution of phosgene in toluene was heated for 8 hours at 100° C. After cooling, the toluene was removed in vacuo and the residue taken up in dichloromethane. The extract was shaken with aqueous sodium hydrogen carbonate and water, dried over magnesium sulfate and concentrated. The residue was recrystallised from isopropanol/diisopropyl ether. Yield: 0.5 g=40% of theory. m.p.: 157°-158° C.

Workup

  1. temperatureAfter cooling
  2. customthe toluene was removed in vacuo
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallised from isopropanol/diisopropyl ether

Sources & evidence

ORD record
ord-493faa9c9345471f9464a36836bbc40e
Source dataset
uspto-grants-1995_06
Patent number
US05424443

Reaction notes

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