Triethylamine → 2,4-dichloro-6-fluoro-7-[N-(2,2-dimethylpropanoyl)hydrazino]benzothiazole

HRID 21733Notes

Reaction equation

HRID 21733 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[S:10][C:11]2[C:17]([NH:18][NH2:19])=[C:16]([F:20])[CH:15]=[C:14]([Cl:21])[C:12]=2[N:13]=1.[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24].C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:8][C:9]1[S:10][C:11]2[C:17]([N:18]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[NH2:19])=[C:16]([F:20])[CH:15]=[C:14]([Cl:21])[C:12]=2[N:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 62493Pivaloyl chlorideHCID 199334672,4-Dichloro-6-fluoro-7-hydrazinobenzothiazole

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.6 ml Triethylamine was added to a solution of 4.8 g 2,4-dichloro-6-fluoro-7-hydrazinobenzothiazole in 38 ml toluene. 2.4 ml Pivaloyl chloride was added dropwise and the mixture stirred for 2 hours at room temperature. It was then treated with ethyl acetate and washed with aqueous sodium hydrogen carbonate and water, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography. Yield: 1.36 g=21% of theory

Workup

  1. washwashed with aqueous sodium hydrogen carbonate and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3507dce14f7b4406b6930ba5b945d4f0
Source dataset
uspto-grants-1995_06
Patent number
US05424443

Reaction notes

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