Methylhydrazine → HCID 14097245, compound

HRID 622211Notes

Reaction equation

HRID 622211 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]=[CH:11][C:10]=1[O:15][CH3:16])=O.[CH3:17][NH:18][NH2:19]>C(O)CO>[CH3:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]1[C:3]2[S:4][CH:5]=[CH:6][C:2]=2[N:18]([CH3:17])[N:19]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 14097218HCID 14097218, compound

Product 1

HCID 14097245HCID 14097245, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of (3-bromothien-2-yl)(2-methoxyphenyl)methanone (10 g), methyl hydrazine (10 ml) and ethylene glycol (70 ml) was stirred at 110°-120° C. for two hours under nitrogen. The reaction mixture was then allowed to cool to room temperature, quenched with 125 ml of water and the organics were extracted into a 50:50 ether/ethyl acetate solution. Washing, drying (over anhydrous magnesium sulfate) and then evaporation of the solvents left 10 g of an oil. This oil was passed through a silica gel column packed in hexane and eluted with dichloromethane to give 7 g of an oil which subsequently crystallized. Recrystallization from ether/hexane gave 4 g of a crystalline solid, m.p. 94°-97° C.

Workup

  1. customquenched with 125 ml of water
  2. extractionthe organics were extracted into a 50:50 ether/ethyl acetate solution
  3. washWashing
  4. dry with materialdrying (over anhydrous magnesium sulfate)
  5. customevaporation of the solvents
  6. waitleft 10 g of an oil
  7. washeluted with dichloromethane

Sources & evidence

ORD record
ord-61415f684b144b78b6123797cb78c4b1
Source dataset
uspto-grants-1988_09
Patent number
US04769472

Reaction notes

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