Tert-Butylamine → 4-(Tert-butylcarbamoyl)-2-methoxybenzenesulphonyl chloride

HRID 1266641Notes

Reaction equation

HRID 1266641 reaction equation
[K+].COC1C=C(C=CC=1S(O)(=O)=O)C([O-])=O.[Cl:17][S:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][C:22]=1[O:30][CH3:31])(=[O:20])=[O:19].[C:32]([NH2:36])([CH3:35])([CH3:34])[CH3:33]>>[CH3:31][O:30][C:22]1[CH:23]=[C:24]([C:25]([NH:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:26])[CH:28]=[CH:29][C:21]=1[S:18]([Cl:17])(=[O:20])=[O:19]

Participants

4

Reactant 3

HCID 6385Tert-ButylamineHCID 104921734-Chlorosulfonyl-3-methoxybenzoyl chlorideHCID 880109973-Methoxy-4-sulfobenzoic acid mono-potassium salt

Product 1

HCID 99265364-(Tert-butylcarbamoyl)-2-methoxybenzenesulphonyl chlorideYield 92%

Procedure

Reacting the 3-methoxy-4-sulfobenzoic acid mono-potassium salt with an inorganic acid halogenide the 4-chlorosulfonyl-3-methoxybenzoyl chloride is obtained. To our surprise we have found that at lower temperature, in an appropriate solvent the t-butylamine reacts selectively with the aromatic acid chloride. Thus, the desired 2-methoxy-4-(N-t-butylaminocarbonyl)benzenesulfonyl chloride is obtained in 92% yield, with a purity of 96%, so it can be used without further purification for the synthesis of drug substances.

Workup

  1. customis obtained

Sources & evidence

ORD record
ord-1148356fbc3f4458a93bd7f6fdbdf4e6
Source dataset
uspto-grants-2003_04
Patent number
US06548702B1

Reaction notes

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