Water → HCID 49783913, compound

HRID 1097212Notes

Reaction equation

HRID 1097212 reaction equation
[OH-].[NH4+:2].[CH3:3][N:4]([N:6]=[N:7][C:8]1[C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C:11]=2[Se:10][C:9]=1[C:17]([O-:19])=O)[CH3:5].O>C1COCC1>[CH3:3][N:4]([N:6]=[N:7][C:8]1[C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C:11]=2[Se:10][C:9]=1[C:17]([NH2:2])=[O:19])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 86646886HCID 86646886, compound

Product 1

HCID 49783913HCID 49783913, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold (0-5° C.) solution of ammonium hydroxide (60 mL) was added a mixture of ethyl and methyl esters of 3-[(dimethylamino)diazenyl]-4,5,6,7-tetrahydrobenzo[2,1-d]selenophene-2-carboxylate (600 mg) in THF (6 mL) for 5 min. A catalytic amount of PEG-400 was added and stirred at rt for 66 h. The solution was poured into ice cooled water and extracted with chloroform (3×150 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 (98:2) as eluents to give the product as a pale brown color solid (100 mg, 18%), which was recrystallized from chloroform-hexane (70 mg), mp 198-202° C. IR (Neat) νmax 3347, 3163, 2932, 2860, 1631, 1342, 1313, 1220, 1103, 1020, 878 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.21 (1H, s, —CONH2), 6.07 (1H, s, —CONH2), 3.51 (3H, br s, —NCH3), 3.14 (3H, br s, —NCH3), 2.80-2.82 (2H, m, H-4), 2.64-2.65 (2H, m, H-7), 1.72-1.80 (4H, m, H-5,6); 13C NMR (100 MHz, CDCl3): δ 165.9, 149.5, 145.9, 132.6, 129.5, 29.0, 28.6, 23.1, 22.7; LC-MS (positive ion mode): m/z 321, 323 (M+Na)+.

Workup

  1. additionA catalytic amount of PEG-400 was added
  2. additionThe solution was poured into ice
  3. extractionextracted with chloroform (3×150 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

Sources & evidence

ORD record
ord-6c9172dc8027488e9f0ab9f8111a8d40
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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