1,1-Dimethylhydrazine → HCID 86747025, compound

HRID 483836Notes

Reaction equation

HRID 483836 reaction equation
[CH3:1][N:2]([CH3:4])[NH2:3].[CH3:5][O:6][CH2:7]/[CH:8]=[CH:9]/[CH:10]=O>>[CH3:1][N:2]([CH3:4])[N:3]=[CH:10]/[CH:9]=[CH:8]/[CH2:7][O:6][CH3:5]

Participants

3

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 108986564-Methoxybut-2-enal

Product 1

HCID 86747025HCID 86747025, compoundYield 78.2%

Procedure

N,N-Dimethylhydrazine (10.90 mL, 0.14 mol) was added dropwise over 15 min to (E)-4-methoxy-2-butenal (13.06 g, 0.13 mol) while cooling the reaction with an ice bath. The bath was then removed and the mixture stirred for 1.5 h at ambient temperature. Calcium chloride (20 g) was added to the reaction, let set for 15 min, and the product decanted. Distillation (bp 102°-110° C., 25 mm Hg) of the oil through a 10 cm Vigreaux column provided pure (E)-4-methoxy-2-butenal N,N-dimethylhydrazone (17) (14.45 g, 78%): IR (neat) 2850, 2820, 1560, 1465, 1445, 1375, 1270, 1120, 1030, 970 cm-1 ; 1H NMR (CDCl3) δ 2.80 (s, 6H), 3.26 (s, 3H), 3.93 (dd, 2H, J=6.2, 1.2 Hz), 5.74 (dt, 1H, J=15.8, 6.2 Hz), 6.31 (ddt, 1H, J=15.8, 8.9, 1.2 Hz), 6.92 (d, 1H, J=8.9 Hz); Anal. calcd for C7H14N2O: C 59.05, H 10.07, N 19.52; found C 59.13, H 9.92, N 19.70.

Workup

  1. temperaturewhile cooling
  2. customthe reaction with an ice bath
  3. customThe bath was then removed
  4. additionCalcium chloride (20 g) was added to the reaction
  5. waitlet set for 15 min
  6. customthe product decanted
  7. distillationDistillation (bp 102°-110° C., 25 mm Hg) of the oil through a 10 cm Vigreaux column

Sources & evidence

ORD record
ord-ab16f12a241b4858b13b238062eae64a
Source dataset
uspto-grants-1993_07
Patent number
US05227383

Reaction notes

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