Hydrochloric Acid → 2-(4-Chloro-phenylsulfonyl)-3-(3,5-dichlorophenylamino)-3-methylsulfanyl-2-propenenitrile

HRID 840206

Reaction equation

HRID 840206 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]#[N:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:20][C:21]1[CH:22]=[C:23]([N:28]=[C:29]=[S:30])[CH:24]=[C:25]([Cl:27])[CH:26]=1.[CH3:31]I.Cl>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11](=[C:29]([NH:28][C:23]2[CH:22]=[C:21]([Cl:20])[CH:26]=[C:25]([Cl:27])[CH:24]=2)[S:30][CH3:31])[C:12]#[N:13])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1387763,5-Dichlorophenyl isothiocyanateHCID 7358292-(4-Chlorobenzenesulfonyl)acetonitrile

Product 1

HCID 701494812-(4-Chloro-phenylsulfonyl)-3-(3,5-dichlorophenylamino)-3-methylsulfanyl-2-propenenitrileYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-chlorophenylsulfonylacetonitrile (1.00 g, 4.6 mmol) in dry acetone (10 ml) first dry potassium carbonate (1.28 g, 9.3 mmol) and then 3,5-dichlorophenyl isothiocyanate (0.99 g, 4.9 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 4 h, and then filtered. To the filtrate methyl iodide (0.86 ml, 13.9 mmol) was added. The mixture was stirred at room temperature for 45 min. Then pH was adjusted to 1 with 1N aqueous HCl. The precipitate was filtered off and washed with water to give 1.86 g (93%) of a crude product. Recrystallisation from ethyl acetatelheptane (1:1) gave 1.42 g (72%) of the title compound contaminated with 4-chlorophenylsulfonylacetonitrile. Mp 128-131° C. 1H NMR (200 MHz, CDCl3): δ=2.25 (s, 3H), 7.20 (d, 2H), 7.30 (t, 1H), 7.55 (d, 2H), 7.85 (d, 2H), 9.80 (br s, 1H); EI SP/MS: 434 (M+), 436 (M+2).

Workup

  1. filtrationfiltered
  2. stirringThe mixture was stirred at room temperature for 45 min
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customto give 1.86 g (93%) of a crude product
  6. customRecrystallisation from ethyl acetatelheptane (1:1)

Sources & evidence

ORD record
ord-b635fff3bd214c52be77837dfb9bd141
Source dataset
uspto-grants-2002_04
Patent number
US06365609B1

Linked notes

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