Methylhydrazine → 3-(3-methoxyphenyl)-1-methyl-1H-thieno[3,2-c]pyrazole

HRID 1787525Notes

Reaction equation

HRID 1787525 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)=O.[CH3:17][NH:18][NH2:19]>C(O)CO>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([C:7]2[C:3]3[S:4][CH:5]=[CH:6][C:2]=3[N:18]([CH3:17])[N:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 21915416(3-Bromothien-2-yl) (3-methoxyphenyl)methanone

Product 1

HCID 140972473-(3-methoxyphenyl)-1-methyl-1H-thieno[3,2-c]pyrazoleYield 55%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Stir a mixture of (3-bromothiophen-2-yl)-(3-methoxyphenyl)methanone (20 g; 0.067 mol.; example 1, step A), ethylene glycol (134 mL) and methylhydrazine (17 g, 0.37 mol) under nitrogen at 120°-130° for 2.5 hours. Cool to room temperature, quench with water (200 mL) and extract with ether (4×200 mL). Dry the combined ether extracts (MgSO4), filter and evaporate the filtrate to an oil. Purify the oil by HPLC (3:1 hexane/ethyl acetate) to give a solid (9 g) and recrystallize from ether to give the title compound as crystals (8.2 g), m.p. 99°-101° C.

Workup

  1. customquench with water (200 mL)
  2. extractionextract with ether (4×200 mL)
  3. dry with materialDry the combined ether
  4. filtrationfilter
  5. customevaporate the filtrate to an oil
  6. customPurify the oil by HPLC (3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ce327f4c243849ea8e296346e43dd706
Source dataset
uspto-grants-2009_03
Patent number
US07511046B2

Reaction notes

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