Benzylamine → 4-(4-Benzylaminosulfonylmethylbenzyl)-nitrobenzene

HRID 723571Notes

Reaction equation

HRID 723571 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[S:10]([CH2:13][C:14]1[CH:29]=[CH:28][C:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[CH:16][CH:15]=1)(=[O:12])=[O:11].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH2:1]([NH:8][S:10]([CH2:13][C:14]1[CH:29]=[CH:28][C:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[CH:16][CH:15]=1)(=[O:11])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 218768184-(4-Chlorosulfonylmethyl-benzyl)-nitrobenzene

Product 1

HCID 218767514-(4-Benzylaminosulfonylmethylbenzyl)-nitrobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzylamine (0.3 mL) was added to a solution of 4-(4-chlorosulfonylmethyl-benzyl)-nitrobenzene (100 mg) in tetrahydrofuran (4 mL). The mixture was stirred for 2 hours, poured into dilute aqueous potassium carbonate, and extracted with dichloromethane (3×15 mL). Solvents were evaporated and the residue was chromatographed on silica gel, eluting with 2% acetone in dichloromethane, to give 4-(4-benzylaminosulfonylmethylbenzyl)-nitrobenzene (44 mg) as a solid.

Workup

  1. extractionextracted with dichloromethane (3×15 mL)
  2. customSolvents were evaporated
  3. customthe residue was chromatographed on silica gel
  4. washeluting with 2% acetone in dichloromethane

Sources & evidence

ORD record
ord-d83b477d04924f26996b78600853b294
Source dataset
uspto-grants-2006_11
Patent number
US07141584B2

Reaction notes

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