Dimethylformamide → 2-(Dimethylamino)ethanesulfonyl chloride

HRID 424671Notes

Reaction equation

HRID 424671 reaction equation
C(Cl)([Cl:3])=O.[CH3:5][N:6]([CH3:13])[CH2:7][CH2:8][S:9]([O-])(=[O:11])=[O:10].[Na+].CN(C=O)C>C(Cl)Cl>[CH3:5][N:6]([CH3:13])[CH2:7][CH2:8][S:9]([Cl:3])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6371PhosgeneHCID 23516383Sodium 2-(dimethylamino)ethanesulfonate

Product 1

HCID 142196572-(Dimethylamino)ethanesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosgene (12 ml, 1M in toluene) was added to a solution of the subtitle product of step i) in DCM (20 ml) and DMF (2.5 ml) and stirred for 3 h before concentrating in vacuo to afford the subtitle compound as an oil that was used directly in the next step. 1H NMR δ(CD3OD) 3.30 (2H, m), 2.80 (2H, m) and 2.31 (6H, s).

Workup

  1. concentrationbefore concentrating in vacuo

Sources & evidence

ORD record
ord-7925932942aa411dabeb858be1dd4ccf
Source dataset
uspto-grants-2012_01
Patent number
US08106063B2

Reaction notes

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