Hydrochloric Acid → 4-[4-(4-Methoxyphenyl)sulfonylaminomethylbenzyl]-nitrobenzene

HRID 2121029Notes

Reaction equation

HRID 2121029 reaction equation
[NH2:1][CH2:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.C(N(CC)CC)C.Cl>ClCCl>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([NH:1][CH2:2][C:3]2[CH:18]=[CH:17][C:6]([CH2:7][C:8]3[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=3)=[CH:5][CH:4]=2)(=[O:29])=[O:28])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 218767314-(4-Aminomethylbenzyl)-nitrobenzene

Product 1

HCID 218768834-[4-(4-Methoxyphenyl)sulfonylaminomethylbenzyl]-nitrobenzeneYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Aminomethylbenzyl)-nitrobenzene (500 mg) was dissolved in dichloromethane (7 mL) and heated with 4-methoxybenzenesulfonyl chloride (426 mg) and triethylamine (0.3 mL). The mixture was stirred at room temperature for 15 hours, poured into dilute aqueous hydrochloric acid, and extracted with dichloromethane (3×). The solvent was evaporated to give 4-[4-(4-methoxyphenyl)sulfonylaminomethylbenzyl]-nitrobenzene as a yellow solid (851 mg, ˜100%), and was used in the next step without further purification.

Workup

  1. extractionextracted with dichloromethane (3×)
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b4df830e48d14878a9d420b93a32524a
Source dataset
uspto-grants-2004_02
Patent number
US06693200B2

Reaction notes

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