Dimethylformamide → N-2-adamantyl-4-[2-(ethylsulfonyl)ethyl]bicyclo[2.2.2]octane-1-carboxamide

HRID 605509Notes

Reaction equation

HRID 605509 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][C:8]12[CH2:15][CH2:14][C:11]([C:16]([OH:18])=O)([CH2:12][CH2:13]1)[CH2:10][CH2:9]2)(=[O:5])=[O:4])[CH3:2].[C:19](Cl)(=O)[C:20](Cl)=O.C[N:26]([CH:28]=O)C>C(Cl)Cl>[CH:20]12[CH2:19][CH:10]3[CH2:9][CH:8]([CH2:13][CH:12]([CH2:11]3)[CH:28]1[NH:26][C:16]([C:11]13[CH2:10][CH2:9][C:8]([CH2:7][CH2:6][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])([CH2:15][CH2:14]1)[CH2:13][CH2:12]3)=[O:18])[CH2:7]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 225917104-[2-(Ethylsulfonyl)ethyl]bicyclo[2.2.2]octane-1-carboxylic acid

Product 1

HCID 11502385N-2-adamantyl-4-[2-(ethylsulfonyl)ethyl]bicyclo[2.2.2]octane-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carboxylic acid 1-4 (810 mg, 3 mmol) was dissolved in methylene chloride (5 ml) and treated with oxalyl chloride (4 eq.) and 0.050 ml of DMF. The reaction was stirred at room temperature for 45 min, then the solvent was removed under reduced pressure to give a quantitative crude yield of 4-[2-(ethylsulfonyl)ethyl]bicyclo[2.2.2]octane-1-carboxyl chloride (1-5).

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-07b8d38533af4560a9c26f88f853ad52
Source dataset
uspto-grants-2011_03
Patent number
US07915252B2

Reaction notes

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