Methylhydrazine → HCID 14097247, compound

HRID 568523Notes

Reaction equation

HRID 568523 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 14097247HCID 14097247, compoundYield 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 The oil
  6. customwas purified by HPLC (3 1 hexane/ethyl acetate) This yielded 9 g of a solid which
  7. customwas recrystallized from ether

Sources & evidence

ORD record
ord-aac7bc8aa5c34c809c163e77aefc1231
Source dataset
uspto-grants-1988_03
Patent number
US04728651

Reaction notes

Loading…