Diethyl Ether → 2-(4-chlorobenzoyl)-N-allylhydrazinecarboxamide

HRID 536535Notes

Reaction equation

HRID 536535 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][NH2:11])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([N:15]=[C:16]=[O:17])[CH:13]=[CH2:14].C(OCC)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][NH:11][C:16]([NH:15][CH2:12][CH:13]=[CH2:14])=[O:17])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 108164-ChlorobenzohydrazideHCID 15123Allyl isocyanate

Product 1

HCID 497656012-(4-chlorobenzoyl)-N-allylhydrazinecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

An amount of 5.00 g (29.3 mmol) of 4-chlorobenzenecarbohydrazide was suspended in dry tetrahydrofuran (150 ml) at 50° C. and then 2.63 ml (29.9 mmol) of allyl isocyanate in solution in 110 ml of dry tetrahydrofuran were added dropwise. The starting material underwent temporary complete dissolution, and then a fine precipitate was produced. The mixture was stirred at 50° C. for 2 hours. After cooling to room temperature it was admixed with diethyl ether. The colourless solid was isolated by suction filtration, washed with diethyl ether and dried in a high vacuum. This gave 7.42 g (100% of theory) of the target compound.

Workup

  1. dissolutionThe starting material underwent temporary complete dissolution
  2. customa fine precipitate was produced
  3. temperatureAfter cooling to room temperature it
  4. customThe colourless solid was isolated by suction filtration
  5. washwashed with diethyl ether
  6. customdried in a high vacuum

Sources & evidence

ORD record
ord-05249b8f506b45a1825876bb1d23e412
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

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