Ethanolamine → N-(2-chloro-5-cyano-3-nitrophenyl)-2-((2-hydroxyethyl)amino)acetamide

HRID 921884Notes

Reaction equation

HRID 921884 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[C:8]([N+:14]([O-:16])=[O:15])[C:7]=1[Cl:17])=[O:4].[NH2:18][CH2:19][CH2:20][OH:21].C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl.C1COCC1>[Cl:17][C:7]1[C:8]([N+:14]([O-:16])=[O:15])=[CH:9][C:10]([C:12]#[N:13])=[CH:11][C:6]=1[NH:5][C:3](=[O:4])[CH2:2][NH:18][CH2:19][CH2:20][OH:21]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 10796Cesium carbonateHCID 899223412-bromo-N-(2-chloro-5-cyano-3-nitrophenyl)acetamide

Product 1

HCID 89922466N-(2-chloro-5-cyano-3-nitrophenyl)-2-((2-hydroxyethyl)amino)acetamideYield 53.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-N-(2-chloro-5-cyano-3-nitrophenyl)acetamide (30 mg, 0.094 mmol) in DCM (2 mL) was added a solution of 2-aminoethanol (5.75 mg, 0.094 mmol) in THF (2 mL) then CESIUM CARBONATE (30.7 mg, 0.094 mmol) was added. After stirring at room temperature for 1.5 h, LC-MS indicated completion. After concentration purification via flash chromatography (0-100% EtOAc in Hexane, 12 g) gave N-(2-chloro-5-cyano-3-nitrophenyl)-2-((2-hydroxyethyl)amino)acetamide as a yellow solid (15 mg).

Workup

  1. concentrationAfter concentration purification via flash chromatography (0-100% EtOAc in Hexane, 12 g)

Sources & evidence

ORD record
ord-970f8c82f1554c478404620194011913
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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