Hydrochloric Acid → alpha-(4-Hydroxybenzenesulfonyloxyimino)thien-2-ylacetonitrile

HRID 648770Notes

Reaction equation

HRID 648770 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:16][N:17]=[C:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)[C:19]#[N:20])(=[O:15])=[O:14])=[CH:9][CH:8]=1)(=O)C.Cl.C(OCC)C>O.O1CCCC1>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:16][N:17]=[C:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)[C:19]#[N:20])(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 54491580alpha-(4-Acetoxybenzenesulfonyloxyimino)thien-2-ylacetonitrile

Product 1

HCID 54023906alpha-(4-Hydroxybenzenesulfonyloxyimino)thien-2-ylacetonitrileYield 68.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

With vigorous stirring, a solution of 12 g of NaOH in 20 ml of water is added to a solution of 27 g (0.08 mole) of α-(4-acetoxybenzenesulfonyloxyimino)thienylacetonitrile (3c) in 125 ml of tetrahydrofuran. After 1 hour, the reaction mixture is acidified with 20% hydrochloric acid and, after the addition of water and diethyl ether, the phases are separated. The aqueous phase is extracted with ether, the combined organic phases are dried over MgSO4, and the solvent is distilled off. The residual crude product is recrystallised from toluene, affording 17 g of beige-coloured crystals which melt at 151°-152° C.

Workup

  1. customthe phases are separated
  2. extractionThe aqueous phase is extracted with ether
  3. dry with materialthe combined organic phases are dried over MgSO4
  4. distillationthe solvent is distilled off
  5. customThe residual crude product is recrystallised from toluene

Sources & evidence

ORD record
ord-fce61e6969264c178e552773f125adb5
Source dataset
uspto-grants-1988_04
Patent number
US04736055

Reaction notes

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