N-methyl-2-pyrrolidone → HCID 67163590, compound

HRID 42341Notes

Reaction equation

HRID 42341 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])=[O:10])=[CH:5][C:4]=1C.BrC1C=CC(S([Cl:28])(=O)=O)=C(Cl)C=1.CN1C(=O)CCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])=[O:10])=[C:5]([Cl:28])[CH:4]=1

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 27347664-Bromo-2-chlorobenzenesulfonyl chlorideHCID 21226445Aluminium lithium hydrideHCID 582753444-Aminomethyl-N-tert-butyl-3-methyl-benzenesulfonamide

Product 1

HCID 67163590HCID 67163590, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

4-Aminomethyl-N-tert-butyl-2-chloro-benzenesulfonamide was synthesized in a manner analogous to 4-Aminomethyl-N-tert-butyl-3-methyl-benzenesulfonamide in Example 4, using 4-bromo-2-chlorobenzene-1-sulfonyl chloride in place of 4-bromo-3-methylbenzene-1-sulfonyl chloride. In the second step NMP was used as the solvent, Pd(dppf)Cl2 alone was used as catalyst and the reaction mixture was stirred at 150° C. for 30 min, then heated at 120° C. overnight. Reduction of the cyano group to aminomethyl group in the last step was achieved by stirring with lithium aluminium hydride from 0° C. to room temperature in THF.

Workup

  1. temperatureheated at 120° C. overnight

Sources & evidence

ORD record
ord-f69782123a1947439e1ac794e0519fd0
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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