Toluene → HCID 178503286, compound

HRID 358212Notes

Reaction equation

HRID 358212 reaction equation
CO[C:3](=[S:9])[C:4]([Cl:8])=C(Cl)C.[C:10](=[O:13])([O-])[O-].[K+].[K+].[CH3:16][NH:17][NH2:18].[C:19]1(C)C=CC=CC=1>>[Cl:8][C:4]1[C:10]([OH:13])=[N:18][N:17]([CH3:16])[C:3]=1[S:9][CH3:19]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6061Methylhydrazine2×HCID 11430Potassium CarbonateHCID 86739596HCID 86739596, compound2×

Product 1

HCID 178503286HCID 178503286, compound

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 11.6 gms (58 mmols) methyl-2,3-dichloro-3-methylthioacrylate (the product of Example 3) and 8.0 gms (58 mmols) potassium carbonate in 150 mls toluene, 2.1 gms (58 mmols) methylhydrazine were added dropwise. The reaction mixture was heated at 80° C. for about 8 hours. Then an additional 0.5 gm methylhydrazine was added; the resulting mixture was heated to reflux and refluxed for 2 hours. The reaction mixture was cooled and then filtered to remove solids. Stripping of the filtrate, followed by chromatography of the residue on silica gel eluting with ethyl acetate, gave 2.8 gms of the product as a solid with a melting point of 163°-165° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux
  3. temperaturerefluxed for 2 hours
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered
  6. customto remove solids

Sources & evidence

ORD record
ord-4e9c7270122c4607bc86aec8db3b645f
Source dataset
uspto-grants-1984_08
Patent number
US04465675

Reaction notes

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