Sodium Hydroxide → 5-Chloro-4-(2,6-dichloroanilino)-3-thiophenacetonitrile

HRID 1680169Notes

Reaction equation

HRID 1680169 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:8]=1[NH:9][C:10]1[C:11]([CH2:15][C:16]#[N:17])=[CH:12][S:13][CH:14]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[Na+]>C(Cl)Cl>[Cl:4][C:14]1[S:13][CH:12]=[C:11]([CH2:15][C:16]#[N:17])[C:10]=1[NH:9][C:8]1[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:7]=1[Cl:6]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 24648Sulfuryl chlorideHCID 23457191HCID 23457191, compound

Product 1

HCID 234572395-Chloro-4-(2,6-dichloroanilino)-3-thiophenacetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 135 mg of sulfuryl chloride in 5 ml of methylene chloride is added dropwise to a solution of 283 mg (1 mmole) of 4-(2,6-dichloroanilino)-3-thiophenacetonitrile in 20 ml of methylene chloride at -15°. After 10 minutes, a sodium dithionite solution and 3 ml of 2 N sodium hydroxide solution are added. The organic phase is separated off, dried, clarified with bleaching earth (for example Tonsil®) and concentrated. Recrystallization of the residue from methanol yields 5-chloro-4-(2,6-dichloroanilino)-3-thiophenacetonitrile (m. 128° to 128.5°).

Workup

  1. customThe organic phase is separated off
  2. customdried
  3. concentrationconcentrated
  4. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-9622c208530749cb818c08e2bcff2570
Source dataset
uspto-grants-1981_06
Patent number
US04272507

Reaction notes

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