Water → N'-t-butyl-N-(4-methylbenzoyl)-N'-(2,5-dichlorothiophene-3-carbonyl)hydrazine

HRID 849786Notes

Reaction equation

HRID 849786 reaction equation
[C:1]([NH:5][NH:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Na+].[Cl:19][C:20]1[S:21][C:22]([Cl:28])=[CH:23][C:24]=1[C:25](Cl)=[O:26]>C1(C)C=CC=CC=1.CCOCC>[C:1]([N:5]([C:25]([C:24]1[CH:23]=[C:22]([Cl:28])[S:21][C:20]=1[Cl:19])=[O:26])[NH:6][C:7](=[O:15])[C:8]1[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 27770842,5-Dichlorothiophene-3-carbonyl chlorideHCID 15452037N'-t-butyl-N-4-methylbenzoylhydrazine

Product 1

HCID 15452005N'-t-butyl-N-(4-methylbenzoyl)-N'-(2,5-dichlorothiophene-3-carbonyl)hydrazine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

N'-t-butyl-N-4-methylbenzoylhydrazine (0.7 g) was dissolved in 35 ml toluene. Water (5 ml) and 50% aqueous sodium hydroxide (0.8 g) were added followed by 2,5-dichlorothiophene-3-carbonylchloride (2.0 g). After stirring for 3 hours at room temperature, ether was added and the organic layer separated. Evaporation afforded a solid which was triturated with 10% ether-hexane to afford N'-t-butyl-N-(4-methylbenzoyl)-N'-(2,5-dichlorothiophene-3-carbonyl)hydrazine. m.p. 163-165° C.

Workup

  1. customthe organic layer separated
  2. customEvaporation
  3. customafforded a solid which
  4. customwas triturated with 10% ether-hexane

Sources & evidence

ORD record
ord-f3124f769396451ba1dee6a3353d5e8e
Source dataset
uspto-grants-2000_01
Patent number
US06013836

Reaction notes

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