Methylhydrazine → HCID 19607529, compound

HRID 1602771Notes

Reaction equation

HRID 1602771 reaction equation
C[NH:2]N.[Br:4][C:5]1[CH:6]=[C:7]([CH3:21])[C:8]2[S:13][CH2:12][C:11](=[CH:14][N:15](C)[CH3:16])[C:10](=O)[C:9]=2[C:19]=1[CH3:20]>C(O)C>[Br:4][C:5]1[CH:6]=[C:7]([CH3:21])[C:8]2[S:13][CH2:12][C:11]3[C:10](=[N:2][N:15]([CH3:16])[CH:14]=3)[C:9]=2[C:19]=1[CH3:20]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 54520283HCID 54520283, compound

Product 1

HCID 19607529HCID 19607529, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.53 mL (0.085 mol) of methyl hydrazine (purchased from Aldrich Chemical Company) was added dropwise to a mixture of 21.54 g (0.066 mol) of the title compound of Step D in 115 mL of ethanol. The mixture was stirred at reflux under nitrogen for 5 hr and was then evaporated to dryness. The crude product was chromatographed over silica gel eluting with a mixture of (1:9) ethyl acetate:hexane to yield two components. Concentration of the major fraction yielded 14.72 g of the title compound of Step E as an oil; 1H NMR (CDCl3): δ2.3 (s,3H), 2.82 (s,3H), 3.76 (s,2H), 3.9 (s,3H), 7.2 (s, 1H), 7.3 (s,1H). Concentration of the minor fraction yielded 3.87 g of the isomer 8-bromo-1,4-dihydro-1,6,9-trimethyl[1]benzothiopyrano[4,3-c]pyrazole as an oil; 1H NMR (CDCl3): δ2.3 (s,3H), 2.46 (s,3H), 3.75 (s,3H), 3.59 and 3.81 (2d,2H), 7.4 (s,1H), 7.45 (s,1H).

Workup

  1. temperatureat reflux under nitrogen for 5 hr
  2. customwas then evaporated to dryness
  3. customThe crude product was chromatographed over silica gel eluting with a mixture of (1:9) ethyl acetate
  4. customhexane to yield two components

Sources & evidence

ORD record
ord-680fc627ed4c4b19b94940ba65217e1f
Source dataset
uspto-grants-1999_11
Patent number
US05985799

Reaction notes

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