Thiophenol → Dimethyl[2-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)ethyl]amine

HRID 31934Notes

Reaction equation

[CH3:1][N:2]([CH3:30])[CH2:3][CH2:4][N:5]([CH2:18][CH2:19][NH:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][N:22]=1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O.C([O-])([O-])=O.[K+].[K+].C1(S)C=CC=CC=1>O.CN(C=O)C>[CH3:1][N:2]([CH3:30])[CH2:3][CH2:4][NH:5][CH2:18][CH2:19][NH:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][N:22]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a suspension of resin-bound [2-(dimethylamino)ethyl]{2-[(5-nitro(2-pyridyl))-amino]ethyl}[(2-nitrophenyl)sulfonyl]amine (3.0 g, 2.1 mmol) and DMF (30 mL) at 23° C. was added H2O (2 drops), K2CO3 (2.9 g, 21 mmol) and PhSH (2.2 mL, 21 mmol). The resulting mixture was shaken at 23° C. for 12 h, filtered, washed with NMP, H2O and CH2Cl2 and air dried to yield polymer-bound dimethyl[2-({2-[(5-nitro(2-pyridyl))amino]-ethyl}amino)ethyl]amine.

Workup

filtrationfiltered
washwashed with NMP, H2O and CH2Cl2 and air
customdried

Sources & evidence

ORD record: ord-6c87d6cbaafc4c1b8b656b6907287d26
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425557B2

Reaction notes

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