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2-Nitrobenzenesulfonyl chloride → {2-[(5-Nitro(2-pyridyl))amino]ethyl}[(2-nitrophenyl)sulfonyl]amine

HRID 31932
Notes
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Reaction equation

HRID 31932 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1.CCN(C(C)C)C(C)C.[N+:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32](Cl)(=[O:34])=[O:33])([O-:25])=[O:24]>C(Cl)Cl>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([NH:4][CH2:3][CH2:2][NH:1][S:32]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N+:23]([O-:25])=[O:24])(=[O:33])=[O:34])=[N:6][CH:7]=1)([O-:13])=[O:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 1224252-(2-Aminoethylamino)-5-nitropyridine

Product 1

HCID 22142870{2-[(5-Nitro(2-pyridyl))amino]ethyl}[(2-nitrophenyl)sulfonyl]amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a suspension of resin-bound (2aminoethyl)(5-nitro(2-pyridyl))amine (30 g, 21 mmol), CH2Cl2 (250 mL) and iPr2NEt (18.3 mL, 105 mmol) at 23° C. was added 2-nitrobenzenesulfonyl chloride (23.3 g, 105 mmol). The resulting mixture was shaken at 23° C. for 6 h, filtered, washed with NMP, H2O and CH2Cl2 and air dried to yield polymer-bound {2-[(5-nitro(2-pyridyl))amino]ethyl}[(2-nitrophenyl)sulfonyl]amine.

Workup

  1. filtrationfiltered
  2. washwashed with NMP, H2O and CH2Cl2 and air
  3. customdried

Sources & evidence

ORD record
ord-ae667c13acff4681a1988d929fc39f58
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425557B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes