Dimethyl Sulfoxide → 4-Methylthio-m-tolyloxyacetonitrile

HRID 66770Notes

Reaction equation

[CH3:1][C:2]1[C:3](C)=[CH:4][C:5]([SH:8])=[CH:6][CH:7]=1.ClC[C:12]#[N:13].[C:14]([O-:17])([O-])=O.[K+].[K+].[CH3:20]S(C)=O>>[CH3:20][S:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[O:17][CH2:14][C:12]#[N:13]

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 7856Chloroacetonitrile

HCID 11430Potassium Carbonate

HCID 877993,4-Xylenethiol

Product 1

HCID 705471844-Methylthio-m-tolyloxyacetonitrile

Procedure

The compound 4-methylthio-m-tolyloxyacetonitrile was prepared substantially as described in previous examples by heating a mixture of 55.0 g of 4-methylthio-m-cresol, 30 g of chloroacetonitrile, 70.7 g of anhydrous K2CO3 and 104 ml of DMSO, which gave 66.0 g of the compound as a reddish oil.

Workup

temperatureby heating

Sources & evidence

ORD record: ord-d13cad06f7ec4a42870381464c0daccd
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04343808

Reaction notes

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