Sodium Hydroxide → HCID 49783989, compound

HRID 1097217Notes

Reaction equation

HRID 1097217 reaction equation
[CH3:1][N:2]([N:4]=[N:5][C:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[Se:8][C:7]=1[C:15]([O-:17])=[O:16])[CH3:3].[OH-].[Na+]>CO.O>[CH3:3][N:2]([N:4]=[N:5][C:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[Se:8][C:7]=1[C:15]([OH:17])=[O:16])[CH3:1]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86646886HCID 86646886, compound

Product 1

HCID 49783989HCID 49783989, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl and methyl esters of 3-[(dimethylamino)diazenyl]-4,5,6,7-tetrahydrobenzo[2,1-d]selenophene-2-carboxylate (1.0 g, 3.1 mmol) prepared as described in Example 5 step c) in methanol (10 mL) was added a solution of sodium hydroxide (500 mg, 12.6 mmol) in water (2 mL) and stirred at rt for 5 h. The mixture was diluted with ice cold water and extracted with chloroform (2×50 mL) to remove impurities. The aqueous layer was acidified with dil. HCl and stirred for 30 min. The solution was extracted with chloroform (3×100 mL) and the combined organic layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent (550 mg, 57%). The crude product was recrystallized from chloroform-diethyl ether to give the product as a dark brown color solid (330 mg), mp 100-102° C. IR (Neat) νmax 3429, 2927, 2855, 1701, 1350, 1110, 1050, 1023, 880 cm−1; 1H NMR (400 MHz, CDCl3): δ 12.71 (1H, br s, —COOH), 3.59 (3H, s, —NCH3), 3.20 (3H, s, —NCH3), 2.83 (2H, t, J=5.4 Hz, H-4), 2.73 (2H, t, J=5.6 Hz, H-7), 1.75-1.81 (4H, m, H-5,6); 13C NMR (100 MHz, CDCl3): δ 164.5, 151.3, 148.9, 131.5, 124.0, 44.1, 36.5, 28.8 (2C), 22.8, 22.4; LC-MS (positive ion mode): m/z 300, 302 (M+H)+.

Workup

  1. additionThe mixture was diluted with ice cold water
  2. extractionextracted with chloroform (2×50 mL)
  3. customto remove impurities
  4. stirringstirred for 30 min
  5. extractionThe solution was extracted with chloroform (3×100 mL)
  6. washthe combined organic layer was washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationThe solution was filtered
  9. customevaporated the solvent (550 mg, 57%)
  10. customThe crude product was recrystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-ddaf9bc714c24c8e9ddd45cf36b55d36
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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