Dimethylformamide → HCID 11694578, compound

HRID 895816Notes

Reaction equation

HRID 895816 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([C:13]([O:15][CH3:16])=[O:14])[C:10](O)=[O:11])[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:19])=O.CN(C)C=O>ClCCCl>[Cl:19][C:10]([CH:9]([CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl Chloride2×HCID 11514264HCID 11514264, compound

Product 1

HCID 11694578HCID 11694578, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A total of 8.0 g of the concentrated residue containing 3-(3′-chlorophenyl)-2-methoxycarbonylpropionic acid prepared in Step B was dissolved in 32.8 g of 1,2-dichloroethane in an atmosphere of nitrogen gas, followed by addition of 11.8 g of thionyl chloride and 0.05 g of dimethylformamide. The mixture was stirred at 40° C. for 7 hours, from which 1,2-dichloroethane and unreacted thionyl chloride were removed under reduced pressure to yield 7.98 g of methyl 2-chloroformyl-3-(3′-chlorophenyl)-propionate. The NMR spectral data of this compound are shown below.

Workup

  1. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-4df52522a2264fe39ecfa55a5dcc45b8
Source dataset
uspto-grants-2005_07
Patent number
US06916946B2

Reaction notes

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