4-Methoxybenzaldehyde → Tert-butyl 3-(4-methoxybenzylidene)carbazate

HRID 597851Notes

Reaction equation

HRID 597851 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])[NH:12][NH2:13]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[N:13]/[NH:12][C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 312444-MethoxybenzaldehydeHCID 70091tert-Butyl carbazate

Product 1

HCID 6876678Tert-butyl 3-(4-methoxybenzylidene)carbazateYield 102%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Add 4-methoxybenzaldehyde (400 g, 2.94 mol) over 20 min to a solution of tert-butyl carbazate (400 g, 2.94 mol) in toluene (750 mL) at 50° C. Heat to reflux over a period of 1 hour (h), collecting water in an azeotrope with the toluene. After no further water is collected, cool to 60° C. Add hexanes until the product precipitates from solution. Cool the bath further to 20° C. Collect the solids by filtration and dry using a nitrogen press to afford the title compound (750.5 g, 91%). 1H NMR [400 MHz, dimethyl sulfoxide-d6 (DMSO-d6)] δ 10.6-10.8 (bs, 1H), 7.88-8.0 (S, 1H), 7.5-7.55 (d, 2H), 6.95-7.0 (d, 2H), 1.45 (s, 9H). ES/MS (m/z): 249 [M-H].

Workup

  1. temperatureHeat
  2. temperatureto reflux over a period of 1 hour (h)
  3. customcollecting water in an azeotrope with the toluene
  4. customAfter no further water is collected
  5. customAdd hexanes until the product precipitates from solution
  6. temperatureCool the bath further to 20° C
  7. customCollect the solids
  8. filtrationby filtration
  9. customdry

Sources & evidence

ORD record
ord-e970d7ef62814bfc9724f96464d27816
Source dataset
uspto-grants-2011_03
Patent number
US07897600B2

Reaction notes

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