Diethyl Ether → 2-(2-phenylbenzoyl)-N-isobutylhydrazinecarboxamide

HRID 660844Notes

Reaction equation

HRID 660844 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([NH:11][NH2:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([N:21]=[C:22]=[O:23])[CH:18]([CH3:20])[CH3:19].C(OCC)C.C1CCCCC1>O1CCCC1>[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([NH:11][NH:12][C:22]([NH:21][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:23])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8078CyclohexaneHCID 612812-Methylpropyl isocyanateHCID 27603652-Phenylbenzhydrazide

Product 1

HCID 486138272-(2-phenylbenzoyl)-N-isobutylhydrazinecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.00 g (4.71 mmol) of 2-phenylbenzoic acid hydrazide are placed in 10 ml tetrahydrofuran at room temperature. 0.51 g (5.15 mmol) of isobutyl isocyanate, dissolved in 2 ml tetrahydrofuran, are rapidly added dropwise with stirring. The mixture is firstly stirred further at room temperature and then allowed to stand overnight. Addition of an equal volume of diethyl ether and 10 ml of cyclohexane results in separation of a small quantity of a solid, which is filtered off and discarded. Concentration of the filtrate yields 1.53 g (ca. 100% of theory) of a slightly THF-moist product, which is used further as such.

Workup

  1. additionare rapidly added dropwise
  2. stirringThe mixture is firstly stirred further at room temperature
  3. customresults in separation of a small quantity of a solid, which
  4. filtrationis filtered off
  5. customConcentration of the filtrate yields 1.53 g (ca. 100% of theory) of a slightly THF-moist product, which

Sources & evidence

ORD record
ord-005a66039c134a6c96c57ede4e85a2c5
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

Loading…