Dimethylformamide → 4-(1,3-Dioxoisoindolin-2-yl)-1-methylcyclohexanecarbonyl chloride

HRID 1944723Notes

Reaction equation

HRID 1944723 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:17][CH2:16][C:15]([CH3:21])([C:18](O)=[O:19])[CH2:14][CH2:13]1.C(Cl)(=O)C([Cl:25])=O.CN(C=O)C>C(Cl)Cl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:17][CH2:16][C:15]([CH3:21])([C:18]([Cl:25])=[O:19])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 580743564-(1,3-Dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylic acid2×

Product 1

HCID 580743734-(1,3-Dioxoisoindolin-2-yl)-1-methylcyclohexanecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(1,3-Dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylic acid (Intermediate 74, 220 mg, 0.786 mmol) was dissolved in DCM (5 mL), and oxalyl chloride (146 mg, 0.1 mL, 1.149 mmol) was added slowly, followed by addition of a drop of DMF. The mixture was stirred at room temperature for 20 min, then concentrated under vacuum to provide the product as a yellow solid that was used as is in the next step.

Workup

  1. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-88e9bf4991074e81bb46feb97be08ec8
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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