Sodium Hydroxide → HCID 23457230, compound

HRID 1680170Notes

Reaction equation

HRID 1680170 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:8]=1[NH:9][C:10]1[C:11]([CH2:15][C:16]([OH:18])=[O:17])=[CH:12][S:13][CH:14]=1.[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:4][C:14]1[S:13][CH:12]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[C:10]=1[NH:9][C:8]1[C:19]([Cl:23])=[CH:20][CH:21]=[CH:22][C:7]=1[Cl:6]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 24648Sulfuryl chlorideHCID 51717Eltenac

Product 1

HCID 23457230HCID 23457230, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.35 g (10 mmoles) of sulfuryl chloride in 20 ml of methylene chloride are added dropwise to a solution of 3.02 g (10 mmoles) of 4-(2,6-dichloroanilino)-3-thiophenacetic acid in 15 ml of methylene chloride at -15°. After 10 minutes, 10 ml each of 2 N NaOH and 10 percent strength (aq) sodium dithionite solution are added. The aqueous phase is separated off, acidified and extracted with ethyl acetate, and the product phase is dried and concentrated. Recrystallization of the residue from cyclohexane yields pure 5-chloro-4-(2,6-dichloroanilino)-3-thiophenacetic acid (d. 141° to 142°).

Workup

  1. customThe aqueous phase is separated off
  2. extractionextracted with ethyl acetate
  3. customthe product phase is dried
  4. concentrationconcentrated
  5. customRecrystallization of the residue from cyclohexane

Sources & evidence

ORD record
ord-f4b8004377964756907e9de4b0b92a0d
Source dataset
uspto-grants-1981_06
Patent number
US04272507

Reaction notes

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