Water → HCID 49783912, compound

HRID 1097208Notes

Reaction equation

HRID 1097208 reaction equation
[OH-].[NH4+:2].[CH3:3][N:4]([N:6]=[N:7][C:8]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[Se:10][C:9]=1[C:17]([O:19]CC)=O)[CH3:5].O>C1COCC1>[CH3:3][N:4]([N:6]=[N:7][C:8]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[Se:10][C:9]=1[C:17]([NH2:2])=[O:19])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 86646883HCID 86646883, compound

Product 1

HCID 49783912HCID 49783912, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold (0-5° C.) solution of ammonium hydroxide (200 mL) was added a solution of ethyl 3-[(dimethylamino)diazenyl]-5-(tert-butyl)selenophene-2-carboxylate (1.2 g) in THF (30 mL) for 5 min and a catalytic amount of PEG-400 was added and stirred at rt for 48 h. The solution was poured into ice cooled water and extracted with chloroform (3×100 mL). The combined organic layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using chloroform-methanol (94:6) as eluents to give the product as a pale brown color solid, which was recrystallized from chloroform-hexane (300 mg, 28%), mp 218-220° C. IR (Neat) νmax 3337, 3156, 2958, 1631, 1602, 1326, 1250, 1219, 1177, 1113, 1006 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.20 (1H, s, —CONH2), 7.41 (1H, s, H-4), 6.01 (1H, br s, —CONH2), 3.56 (3H, s, —NCH3), 3.16 (3H, s, —NCH3), 1.37 (9H, s, t-butyl); 13C NMR (100 MHz, DMSO-d6): δ 168.0, 166.1, 151.1, 129.0, 116.9, 36.8, 32.4; LC-MS (positive ion mode): m/z 323, 325 (M+Na)+.

Workup

  1. additiona catalytic amount of PEG-400 was added
  2. additionThe solution was poured into ice
  3. extractionextracted with chloroform (3×100 mL)
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered
  7. customevaporated the solvent
  8. customThe residue was chromatographed over silica gel column
  9. customto give the product as a pale brown color solid, which
  10. customwas recrystallized from chloroform-hexane (300 mg, 28%), mp 218-220° C

Sources & evidence

ORD record
ord-d71d4a79c3194a4eb44666ffab2e8684
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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