Hydrochloric Acid → 2(3H)-Thiazolethione, 4-(chloromethyl)-3-(2,3,4-trifluorophenyl)-
Reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[S:18])[S:12][CH2:13][C:14](=O)[CH2:15][Cl:16].Cl.S(=O)(=O)(O)O>C(O)C>[Cl:16][CH2:15][C:14]1[N:10]([C:3]2[CH:4]=[CH:5][C:6]([F:9])=[C:7]([F:8])[C:2]=2[F:1])[C:11](=[S:18])[S:12][CH:13]=1Participants
Procedure
That is, first the known compound (XIV)(see European patent publication No. 286089) is reacted with 1,3-dichloroacetone in an organic solvent such as chloroform, methylene chloride or a lower alcohol to produce 3-chloro-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamate (XV). The compound (XV) is then heated with an inorganic acid such as hydrochloric acid or sulfuric acid in a lower alcohol such as ethanol to give 4-chloromethyl-3-(2,3,4-trifluorophenyl)-2(3H)-1,3-thiazolethione (XVI). The compound (XVI) is then reacted with methylamine in an aprotic organic solvent such as N,N-dimethylformamide or acetonitrile to give 1H,4H-thiazolo[3,4-a]quinoxaline-1-thione derivative (XVII). The compound (XVII) is then reacted with a lower alkyl iodide in a polar solvent such as N,N-dimethylformamide, acetonitrile or ethanol to give a 1-(lower alkyl)thioquinoxalino[1,2-c]thiazolium iodide (XVIII). Then the compound (XVIII) is reacted with a di(lower alkyl) malonate sodium, which is prepared from di(lower alkyl) malonate and sodium hydride, in an organic solvent such as tetrahydrofuran or dioxane to give di(lower alkyl) (1H,4H-thiazolo[3,4-a]quinoxalin-1-ylidene)malonate (X).
Sources & evidence
- ORD record
- ord-f3b01e8dcea4432cbbfac8dd66e42e37
- Source dataset
- uspto-grants-1990_11
- Patent number
- US04971967
Reaction notes
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