1-Bromo-2-methylpropane → 2-chloro-N-isobutyl-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-benzenesulfonamide

HRID 1665013Notes

Reaction equation

HRID 1665013 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][CH2:12][C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=2)=[CH:16][CH:17]=1)(=[O:10])=[O:9].[H-].[Na+].Br[CH2:31][CH:32]([CH3:34])[CH3:33]>CN(C)C(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:12][C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=2)=[CH:16][CH:17]=1)(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 674405452-chloro-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-benzenesulfonamide

Product 1

HCID 252341782-chloro-N-isobutyl-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In analogy to example 1, step 2, 2-chloro-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-benzenesulfonamide (example 4, step 2) was reacted with sodium hydride in N,N-dimethylacetamide at 0° C. followed by reaction with 1-bromo-2-methylpropane at r.t. overnight to give 2-chloro-N-isobutyl-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-benzenesulfonamide as an off-white solid. MS: 515.3 ([M+NH4]+)

Sources & evidence

ORD record
ord-a5f5d6250ea94d19852ac90723e49595
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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