Diethyl Ether → 2-(3-bromobenzoyl)-N-isobutylhydrazinecarboxamide

HRID 660843

Reaction equation

HRID 660843 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][NH2:8])=[O:6].[CH2:12]([N:16]=[C:17]=[O:18])[CH:13]([CH3:15])[CH3:14].C(OCC)C>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][NH:8][C:17]([NH:16][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:18])=[O:6]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 612812-Methylpropyl isocyanateHCID 520941m-Bromobenzohydrazide

Product 1

HCID 474281672-(3-bromobenzoyl)-N-isobutylhydrazinecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.00 g (23.3 mmol) of 3-bromobenzoic acid hydrazide are placed in 50 ml tetrahydrofuran at room temperature. 2.70 g (27.2 mmol) of isobutyl isocyanate, dissolved in 10 ml tetrahydrofuran, are rapidly added dropwise with stirring to this suspension. The mixture is firstly further stirred at room temperature and then allowed to stand overnight. The precipitate formed after addition of 100 ml diethyl ether is filtered off and then washed with diethyl ether. An initial quantity of 1.42 g (19% of theory) of the target compound is thus obtained. The mother liquor is concentrated, and the residue again slurried in diethyl ether and filtered. After washing with diethyl ether and drying in vacuo, a further 5.62 g (77% of theory) of the target compound remain.

Workup

  1. additionare rapidly added dropwise
  2. stirringThe mixture is firstly further stirred at room temperature
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. washwashed with diethyl ether
  6. customAn initial quantity of 1.42 g (19% of theory) of the target compound is thus obtained
  7. concentrationThe mother liquor is concentrated
  8. filtrationfiltered
  9. washAfter washing with diethyl ether
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-3f37f4fe9ad4464197e67393f814bb5e
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Linked notes

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