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

HRID 622226Notes

Reaction equation

HRID 622226 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 49.9%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 20 g of (3-bromothien-2-yl) (3-methoxyphenyl)methanone and 17 g of methyl hydrazine in 134 ml of ethylene glycol was stirred under nitrogen at 120°-130° C. The reaction was complete in 2.5 hours. The product was allowed to cool to room temperature, and thereafter quenched with water (200 ml) and extracted with ether (4×200 ml). The organics were dried over anhydrous magnesium sulfate and the solvents were evaporated to give an oil. The oil was purified by HPLC (3:1 hexane/ethyl acetate). This yielded 9 g of a solid which was recrystallized from ether to give 8.2 g of crystals, mp 99°-101° C.

Workup

  1. customquenched with water (200 ml)
  2. extractionextracted with ether (4×200 ml)
  3. dry with materialThe organics were dried over anhydrous magnesium sulfate
  4. customthe solvents were evaporated
  5. customto give an oil
  6. customThe oil was purified by HPLC (3:1 hexane/ethyl acetate)
  7. customThis yielded 9 g of a solid which was recrystallized from ether

Sources & evidence

ORD record
ord-602eb3d7cb1146d393a85162a5cceabc
Source dataset
uspto-grants-1988_09
Patent number
US04769472

Reaction notes

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