Sulfuric Acid → Ethyl 3-[1-(4-chlorophenyl)-2,2-dimethylpropylidene]carbazate

HRID 703668Notes

Reaction equation

HRID 703668 reaction equation
[C:1]([C:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=O)([CH3:4])([CH3:3])[CH3:2].[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[NH:15][NH2:16].S(=O)(=O)(O)O>C(O)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5](=[N:16][NH:15][C:14]([O:18][CH2:19][CH3:20])=[O:17])[C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 111380501-(4-Chlorophenyl)-2,2-dimethylpropan-1-one

Product 1

HCID 53994370Ethyl 3-[1-(4-chlorophenyl)-2,2-dimethylpropylidene]carbazate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.92 g (0.025 mol) 4-chlorphenyl tert.-butyl ketone and 8.05 g (0.075 mol) ethyl carbazate in 125 ml absolute ethanol was treated with ca. 0.3 g concentrated sulphuric acid and heated at reflux for 3 hours. The solution was then concentrated in vacuo and the residue added to water. It was then extracted with ethyl acetate, the organic phase dried with magnesium sulphate, concentrated and the residue recrystallised from diisopropyl ether.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. concentrationThe solution was then concentrated in vacuo
  4. additionthe residue added to water
  5. extractionIt was then extracted with ethyl acetate
  6. dry with materialthe organic phase dried with magnesium sulphate
  7. concentrationconcentrated
  8. customthe residue recrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-d9e7f4b6bca34aa7ab11a26279a49207
Source dataset
uspto-grants-1991_01
Patent number
US04983755

Reaction notes

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