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

HRID 714611Notes

Reaction equation

HRID 714611 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([N:15]=[C:16]=[O:17])[CH:13]=[CH2:14].C(OCC)C>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH:9][C:16]([NH:15][CH2:12][CH:13]=[CH2:14])=[O:17])=[O:7])=[CH:4][CH:3]=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

At 50° C., 5.00 g (29.3 mmol) of 4-chlorobenzohydrazide were suspended in 150 ml of dry THF. 2.63 ml (29.9 mmol) of allyl isocyanate, dissolved in 110 ml of dry THF, were then added dropwise. Initially, all of the starting material dissolved, and then a fine precipitate formed. The mixture was stirred at 50° C. for 2 h. After cooling to room temperature, diethyl ether was added. The colorless solid was filtered off with suction, washed with diethyl ether and dried under high vacuum. This gave 7.42 g (100% of theory) of the target compound.

Workup

  1. customAt 50° C.
  2. additionwere then added dropwise
  3. dissolutionInitially, all of the starting material dissolved
  4. customa fine precipitate formed
  5. temperatureAfter cooling to room temperature
  6. filtrationThe colorless solid was filtered off with suction
  7. washwashed with diethyl ether
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-f1cbbec94f9a414086d5046acea85ba5
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

Loading…