Hydrochloric Acid → HCID 22418338, compound

HRID 2082102Notes

Reaction equation

HRID 2082102 reaction equation
N(OC(C)(C)C)=O.[Cl:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([Cl:19])[C:10]=1[N:20]1[C:24]([Cl:25])=[C:23]([C:26]#[N:27])[C:22]([S:28][C:29]([F:32])([F:31])[F:30])=[C:21]1N.[ClH:34].[C:35](#[N:38])[CH:36]=[CH2:37]>C(#N)C>[Cl:19][C:11]1[CH:12]=[C:13]([C:15]([F:16])([F:18])[F:17])[CH:14]=[C:9]([Cl:8])[C:10]=1[N:20]1[C:24]([Cl:25])=[C:23]([C:26]#[N:27])[C:22]([S:28][C:29]([F:30])([F:31])[F:32])=[C:21]1[CH2:37][CH:36]([Cl:34])[C:35]#[N:38]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7855AcrylonitrileHCID 10906Tert-Butyl nitriteHCID 22418358HCID 22418358, compound

Product 1

HCID 22418338HCID 22418338, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 2.90 g (21.6 mmoles) of cupric chloride in a mixture of 20 mL of acetonitrile and 40 mL of acrylonitrile was added 2.73 mL (2.37 g, 23.0 mmoles) of t-butyl nitrite. The resulting black solution was cooled to 0° C. and a solution of 6.66 g (14.7 mmoles) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-2-amino-3-trifluoromethylthio-4-cyano-5-chloropyrrole prepared according to EXAMPLE 8 in 25 mL of acetonitrile was added dropwise and with stirring over a period of 20 minutes. The mixture was allowed to stir for 4 hours at room temperature and was then poured into 400 mL of 1N aqueous HCl and partitioned successively with dichloromethane and water. The organic extracts were dried over anhydrous MgSO4 and concentrated. The residual brown oil was chromatographed on silica gel eluting initially with 2:1 and then 1:1 v/v dichloromethane-hexane to give 5.30 g (69%) of 1 -(2,6-dichloro-4-trifluoromethylphenyl)-2-(2-chloro-2-cyanoethyl)-3-trifluoromethylthio-4-cyano-5-chloropyrrole.

Workup

  1. additionwas added dropwise
  2. stirringto stir for 4 hours at room temperature
  3. custompartitioned successively with dichloromethane and water
  4. dry with materialThe organic extracts were dried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residual brown oil was chromatographed on silica gel eluting initially with 2:1

Sources & evidence

ORD record
ord-18403a38d0d04ab185f05e1f633918a1
Source dataset
uspto-grants-1993_02
Patent number
US05187185

Reaction notes

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