Ethanolamine → HCID 59237159, compound

HRID 2380795Notes

Reaction equation

HRID 2380795 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[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>C1COCC1>[CH3:7][N:6]([N:8]=[N:9][C:10]1[CH:14]=[CH:13][S:12][C:11]=1[C:15]([NH:4][CH2:3][CH2:1][OH:2])=[O:16])[CH3:5]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 962WaterHCID 16639509HCID 16639509, compound

Product 1

HCID 59237159HCID 59237159, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cold (0-5° C.) solution of ethanol amine (5 mL) in THF (5 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (500 mg) in THF (5 mL) for 5 min and stirred at rt for 20 h. The solution was poured into ice cooled water and the solution was extracted with ethyl acetate (3×50 mL). The combined EtOAc 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 (95:5) as eluents to give the product, which was recrystallized from chloroform-hexane gave the product as a pale orange color solid (430 mg, 77%), mp 118-122° C. IR (neat) νmax, 3397, 3278, 2926, 1621, 1353, 1298, 1220, 1083, 1007, 882, 775 cm−1;

Workup

  1. additionThe solution was poured into ice
  2. extractionthe solution was extracted with ethyl acetate (3×50 mL)
  3. washThe combined EtOAc layer was washed with water, 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
  8. customto give the product, which
  9. customwas recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-b072bf7efd5d47879a138356d9c0935f
Source dataset
uspto-grants-2012_09
Patent number
US08258119B2

Reaction notes

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