Triethylamine → HCID 89535889, compound

HRID 706341Notes

Reaction equation

HRID 706341 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:3]=1[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.[C:27](Cl)(=[O:30])[CH:28]=[CH2:29]>C(Cl)Cl>[C:27]([NH:1][C:2]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:3]=1[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:30])[CH:28]=[CH2:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 682460781225193-84-9

Product 1

HCID 89535889HCID 89535889, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 2-amino-5-nitrobenzylcarbamate (200 mg, 0.75 mmol) and triethylamine (76 mg, 0.75 mmol) in DCM was added acryloyl chloride (102 mg, 1.12 mmol). The mixture was stirred at rt for 48 h, and purified with column chromatography to give tert-butyl 2-acrylamido-5-nitrobenzylcarbamate. The tert-butyl 2-acrylamido-5-nitrobenzylcarbamate was dissolved in EtOH/HCl and stirred at rt for 1 h. Diethyl ether was then added and the solid formed was collected by filtration to yield the HCl salt of N-(2-(aminomethyl)-4-nitrophenyl)acrylamide (46 mg, 0.18 mmol).

Workup

  1. custompurified with column chromatography

Sources & evidence

ORD record
ord-e837f649e38f40309f24fc38072de784
Source dataset
uspto-grants-2015_11
Patent number
US09174984B2

Reaction notes

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