Ethanol → 3-Amino-5-tert-butylselenophene-2-carboxamide

HRID 1529830Notes

Reaction equation

HRID 1529830 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[Se:4][C:3]=1[C:11]#[N:12].C([OH:15])C>[OH-].[Na+]>[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:9])([CH3:8])[CH3:10])[Se:4][C:3]=1[C:11]([NH2:12])=[O:15]

Participants

4

Reactant 2

HCID 702EthanolHCID 595472203-Amino-5-(tert-butyl)selenophene-2-carbonitrile

Product 1

HCID 866468893-Amino-5-tert-butylselenophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
7.5 °C

Procedure

To a suspension of 3-amino-5-(tert-butyl)selenophene-2-carbonitrile (2.0 g) in aqueous sodium hydroxide solution (50 mL, 10%) was added ethanol (50 mL) and the mixture refluxed for 1 h. Ethanol was distilled off under vacuum and the mixture was allowed to cool to 5-10° C. The separated crystals were filtered off, washed with cold water and dried to give the product as an off-white color solid (1.8 g, 83%), mp 160-162° C. (Hesse, S.; Chenet, C.; Thomae, D.; Kirsch, G. Synthesis, 2009, 1204-1208). 1H NMR (400 MHz, CDCl3): δ 6.58 (1H, s), 5.75 (2H, br s), 5.13 (2H, br s), 1.34 (9H, s).

Workup

  1. temperaturethe mixture refluxed for 1 h
  2. distillationEthanol was distilled off under vacuum
  3. filtrationThe separated crystals were filtered off
  4. washwashed with cold water
  5. customdried
  6. customto give the product

Sources & evidence

ORD record
ord-8277906799ee4b1f8161835cf60c5cfe
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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