Oxalyl chloride → (Z)-1-(4-Methylsulfonylbenzylidene)-5-dimethylamino-2-methyl-3-indenylacetyl chloride

HRID 377759

Reaction equation

HRID 377759 reaction equation
[CH3:1][S:2]([C:5]1[CH:28]=[CH:27][C:8](/[CH:9]=[C:10]2/[C:11]([CH3:26])=[C:12]([CH2:22][C:23](O)=[O:24])[C:13]3[C:18]/2=[CH:17][CH:16]=[C:15]([N:19]([CH3:21])[CH3:20])[CH:14]=3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(Cl)(=O)C([Cl:32])=O>C1COCC1>[CH3:1][S:2]([C:5]1[CH:28]=[CH:27][C:8](/[CH:9]=[C:10]2/[C:11]([CH3:26])=[C:12]([CH2:22][C:23]([Cl:32])=[O:24])[C:13]3[C:18]/2=[CH:17][CH:16]=[C:15]([N:19]([CH3:21])[CH3:20])[CH:14]=3)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 70288307(Z)-1-(p-methylsulfonylbenzylidene)-5-dimethylamino-2-methyl-3-indenylacetic acid

Product 1

HCID 86755163(Z)-1-(4-Methylsulfonylbenzylidene)-5-dimethylamino-2-methyl-3-indenylacetyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Z)-1-(p-methylsulfonylbenzylidene)-5-dimethylamino-2-methyl-3-indenylacetic acid (70 mmol) in THF (500 ml) is allowed to react with oxalylchloride (2 M in CH2Cl2 ; 70 mmol) under reflux conditions (24 hours). The solvent is evaporated to yield the title compound, which is used as such in the next step.

Workup

  1. customThe solvent is evaporated

Sources & evidence

ORD record
ord-e2929b27588e4b1888b43b4c40832e59
Source dataset
uspto-grants-2000_02
Patent number
US06028116

Linked notes

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