1-Propanol → 3,4-Dichloro-α-oxobenzeneacetonitrile

HRID 2269609Notes

Reaction equation

HRID 2269609 reaction equation
[C:1]([NH:4][N:5]=[C:6]([C:15]#[N:16])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)(=[NH:3])[NH2:2].C([OH:20])CC>CS(C)=O>[NH2:3][C:1]1[N:4]=[N:5][C:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=2)=[C:15]([NH2:16])[N:2]=1.[Cl:14][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[Cl:13])[C:6]([C:15]#[N:16])=[O:20]

Participants

5

Reactant 2

HCID 10311-PropanolHCID 178511375HCID 178511375, compound

Product 2

HCID 99424223,4-Dichloro-α-oxobenzeneacetonitrileHCID 15332575HCID 15332575, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared as in Example 2(a) from 3,4-dichlorobenzoyl cyanide amidinohydrazone obtained in Example 5. The solvent for the ring closure was a mixture of 1-propanol and dimethyl sulfoxide (11). Total yield (from 3,4-dichlorobenzoyl cyanide): 76%; m.p. 222-224° C. (uncorrected).

Sources & evidence

ORD record
ord-8906e27b682a47089df44c86ffdcf4bf
Source dataset
uspto-grants-2001_12
Patent number
US06329521B2

Reaction notes

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