Water → HCID 59237158, compound

HRID 2380797Notes

Reaction equation

HRID 2380797 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[CH3:5][N:6]([N:8]=[N:9][C:10]1[CH:14]=[CH:13][S:12][C:11]=1[C:15](OC)=[O:16])[CH3:7].O.[Cl-].[Na+]>C(O)C>[NH2:3][CH2:2][CH2:1][NH:4][C:15]([C:11]1[S:12][CH:13]=[CH:14][C:10]=1[N:9]=[N:8][N:6]([CH3:7])[CH3:5])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 5234Sodium ChlorideHCID 16639509HCID 16639509, compound

Product 1

HCID 59237158HCID 59237158, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To an ice cold (0-5° C.) solution of ethylenediamine (5 mL) in ethanol (5 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (250 mg) in ethanol (5 mL) for 5 min and stirred at rt for 24 h. The solution was poured into ice cooled water and saturated with sodium chloride. The solution was extracted with THF (3×100 mL). The combined THF layer was washed with 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 (90:10) as eluents to give the product as an off-white solid (60 mg, 22%), mp 98-100° C. 1H NMR (400 MHz, CDCl3): δ 8.65 (1H, br s), 7.30 (1H, d, J=5.2 Hz), 7.28 (1H, d, J=5.2 Hz), 3.50-3.57 (5H, m). 3.24 (3H, br s), 2.91 (2H, t, J=6.0 Hz).

Workup

  1. additionThe solution was poured into ice
  2. extractionThe solution was extracted with THF (3×100 mL)
  3. washThe combined THF layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. customevaporated the solvent
  7. customThe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-7c5be783ec6242c6a6814b392b7e3fcb
Source dataset
uspto-grants-2012_09
Patent number
US08258119B2

Reaction notes

Loading…