Hydrochloric Acid → HCID 22418338, compound

HRID 1720457Notes

Reaction equation

HRID 1720457 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 anydrous 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 anydrous MgSO4
  5. concentrationconcentrated
  6. customThe residual brown oil was chromatographed on silica gel eluting initially with 2:1

Sources & evidence

ORD record
ord-193cdadd30084dda8a82f2f94a652ec1
Source dataset
uspto-grants-1996_04
Patent number
US05506260

Reaction notes

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