1,1-Dimethylhydrazine → 1,1-Dimethyl-4-(O-tolyl)semicarbazide

HRID 1601133Notes

Reaction equation

HRID 1601133 reaction equation
[C:1]1([CH3:10])[C:2]([N:7]=[C:8]=[O:9])=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:11][N:12]([CH3:14])[NH2:13]>C1(C)C=CC=CC=1>[CH3:11][N:12]([CH3:14])[NH:13][C:8]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:10])=[O:9]

Participants

4

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 691942-Tolyl isocyanate

Product 1

HCID 46125821,1-Dimethyl-4-(O-tolyl)semicarbazide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
5 °C

Procedure

o-Tolyl isocyanate (10.0 g) was dissolved in 75 mL toluene under N2. The solution was cooled to 5° C. and to this was slowly added a solution in toluene of 1,1-dimethylhydrazine (5.7 mL). After addition, the ice-bath was removed and the resulting slurry allowed to stir an additional 10 minutes. The solid was filtered off rinsing successively with hexane, a small amount of 20% diethylether/hexane, then hexanes again. This afforded 11.1 g (77%) of the title compound of Step A. 1H NMR (CDCl3) δ 8.1 (bs,1H), 7.94 (d,1H) 7.21-7.15 (m,3H), 6.99 (t,1H), 5.23 (bs,1H), 2.63 (s,6H), 2.27 (s,3H).

Workup

  1. additionAfter addition
  2. customthe ice-bath was removed
  3. filtrationThe solid was filtered off
  4. washrinsing successively with hexane

Sources & evidence

ORD record
ord-8dc6b06ecd19435eba6fbb7be9533053
Source dataset
uspto-grants-1999_11
Patent number
US05977149

Reaction notes

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