Ammonia → HCID 136378637, compound

HRID 2408981Notes

Reaction equation

HRID 2408981 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]([NH2:13])=[O:12].S(=O)(=O)(O)O.N.[CH:20](O)=O>>[C:7]([C:5]1[Se:4][C:3]2[C:11](=[O:12])[NH:13][CH:20]=[N:1][C:2]=2[CH:6]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 284Formic AcidHCID 1118Sulfuric AcidHCID 866468893-Amino-5-tert-butylselenophene-2-carboxamide

Product 1

HCID 136378637HCID 136378637, compoundYield 80%

Procedure

To a solution of 3-amino-5-(tert-butyl)selenophene-2-carboxamide (1 g) in formic acid (10 mL) was added concentrated sulfuric acid (5 mL) slowly for 10 min at rt. The mixture was refluxed for 1.5 h and allowed to rt. The mixture was poured into ice cold water and basified with ammonia solution. The solution was extracted with chloroform (3×200 mL) and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent to give the product as a yellow color solid (900 mg, 80%), mp 240-242° C. 1H NMR (400 MHz, CDCl3): δ 12.61 (1H, br s), 8.16 (1H, s), 7.34 (1H, s), 1.46 (9H, s); LC-MS (negative ion mode): m/z 253, 255 (M−H)−.

Workup

  1. temperatureThe mixture was refluxed for 1.5 h
  2. customallowed to rt
  3. additionThe mixture was poured into ice cold water
  4. extractionThe solution was extracted with chloroform (3×200 mL)
  5. washthe combined chloroform layer was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution was filtered
  8. customevaporated the solvent

Sources & evidence

ORD record
ord-4b1ddc0da939427fa914a5e40e801550
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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