Sodium Hydroxide → alpha-(4-Hydroxybenzenesulfonyloxyimino)benzyl cyanide

HRID 648772Notes

Reaction equation

HRID 648772 reaction equation
ON=C(C#N)C1C=CC=CC=1.OC1C=CC(S(ON=C(C2SC=CC=2)C#N)(=O)=O)=CC=1.C([O:35][C:36]1[CH:41]=[CH:40][C:39]([S:42]([O:45][N:46]=[C:47]([C:54]#[N:55])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)(=[O:44])=[O:43])=[CH:38][CH:37]=1)(=O)C.[OH-].[Na+]>>[OH:35][C:36]1[CH:41]=[CH:40][C:39]([S:42]([O:45][N:46]=[C:47]([C:54]#[N:55])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)(=[O:44])=[O:43])=[CH:38][CH:37]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 699982-(Hydroxyimino)-2-phenylacetonitrileHCID 54023906alpha-(4-Hydroxybenzenesulfonyloxyimino)thien-2-ylacetonitrileHCID 54392200alpha-(4-Acetoxybenzenesulfonyloxyimino)benzyl cyanide

Product 1

HCID 54313704alpha-(4-Hydroxybenzenesulfonyloxyimino)benzyl cyanide

Procedure

14.6 g (0.1 mole) of α-hydroxyiminobenzyl cynide (1c) are reacted with 23.46 g (0.1 mole) of 4-acetoxybenzenesulfonyl chloride (3a) in accordance with a procedure analogous to that of Example 3c. The resultant α-(4-acetoxybenzenesulfonyloxyimino)benzyl cyanide melts at 142°-143° C. 6 g of this compound are hydrolysed with a solution of NaOH in accordance with a procedure analogous to that of Example 3d, affording the title compound which, after recrystalisation from toluene, melts at 148° C.

Sources & evidence

ORD record
ord-d4e33870488b4c2ca35fa36f755328bd
Source dataset
uspto-grants-1988_04
Patent number
US04736055

Reaction notes

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