Thionyl Chloride → HCID 69592852, compound

HRID 1062013Notes

Reaction equation

HRID 1062013 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:12])=[C:7]([CH:11]=1)[C:8](Cl)=[O:9])#[N:2].O=S(Cl)Cl.[K+].[C:18]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:19]C([O-])=O.[Mg+2].[Cl-].[Cl-]>C1(C)C=CC=CC=1.CC#N.CCN(CC)CC.CN(C=O)C>[CH2:25]([O:24][C:18](=[O:23])[CH2:19][C:8]([C:7]1[CH:11]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=1[F:12])=[O:9])[CH3:26]

Participants

9

Reactant 4

HCID 24386Thionyl ChlorideHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium ChlorideHCID 21942520HCID 21942520, compound

Product 1

HCID 69592852HCID 69592852, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

Prepared from 5-cyano-2-fluoro-benzoyl chloride [prepared from the corresponding acid [CAS-No. 146328-87-21 by treatment with SOCl2, cat. DMF in toluene at 80° C.] by reaction with ethyl malonate potassium salt with Et3N and MgCl2 in CH3CN according to general procedure H (method a). Obtained as a light yellow solid (3.85 g).

Sources & evidence

ORD record
ord-f4881c15aee14828b17d0d49d86df0fa
Source dataset
uspto-grants-2005_11
Patent number
US06960578B2

Reaction notes

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