Water → HCID 49783911, compound

HRID 1097205Notes

Reaction equation

HRID 1097205 reaction equation
[OH-].[NH4+:2].[CH3:3][N:4]([N:6]=[N:7][C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[Se:10][C:9]=1[C:19]([O:21]CC)=O)[CH3:5].O>C1COCC1>[CH3:3][N:4]([N:6]=[N:7][C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[Se:10][C:9]=1[C:19]([NH2:2])=[O:21])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 86646881HCID 86646881, compound

Product 1

HCID 49783911HCID 49783911, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold (0-5° C.) solution of ammonium hydroxide (160 mL) was added a solution of ethyl 3-[(dimethylamino)diazenyl]-5-phenylselenophene-2-carboxylate (1.2 g) in THF (25 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 off-white solid, which was recrystallized from chloroform-hexane (270 mg, 31%), mp 222-224° C. IR (Neat) νmax 3346, 2927, 2850, 1645, 1594, 1221, 1113, 1019, 875, 850 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.25 (1H, s, —CONH2), 7.87 (1H, s, H-4), 7.57-7.60 (2H, m, Ar—H), 7.30-7.40 (3H, m, Ar—H), 6.18 (1H, br s, —CONH2), 3.58 (3H, s, —N—CH3), 3.19 (3H, s, —N—CH3); 13C NMR (100 MHz, DMSO-d6): δ 165.6, 152.1, 151.9, 136.1, 131.1, 128.9, 128.5, 126.2, 118.1, 43.7, 36.6; LC-MS (positive ion mode): m/z 343, 345 (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

Sources & evidence

ORD record
ord-b3863a054d5e4646bfb66c866d6c880e
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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