Beta-Alanine → HCID 53937509, compound

HRID 247866Notes

Reaction equation

HRID 247866 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:14][CH3:15])[C:12]=1[OH:13])[CH:8]=O)[CH3:3].[S:16]1[CH2:22][C:20](=[O:21])[NH:19][C:17]1=[S:18].NCCC(O)=O>C(O)(=O)C>[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:8]=[C:22]2[S:16][C:17](=[S:18])[NH:19][C:20]2=[O:21])[CH:10]=[C:11]([O:14][CH3:15])[C:12]=1[OH:13])[CH3:3]

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 1201546RhodanineHCID 14877773-[(Dimethylamino)methyl]-4-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 53937509HCID 53937509, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-[(dimethylamino)methyl]-4-hydroxy-5-methoxybenzaldehyde (2.5 g, 12 mmoles), rhodanine (1.6 g, 12 mmoles), β-alanine (0.6 g, 7 mmoles), and acetic acid (35 ml) is stirred under an inert atmosphere and heated to reflux. After 4 hours the acetic acid is removed by rotary evaporator and the residue dissolved in water (250 ml). The solution is brought to approximate neutrality by addition of saturated aqueous sodium bicarbonate, and stirred for 3 hours. The precipitate is filtered off, rinsed three times with water and dried, then triturated in boiling methanol (100 ml), cooled, filtered off and dried to afford the pure product (2.9 g), mp 198° C. (dec).

Workup

  1. temperatureheated to reflux
  2. customAfter 4 hours the acetic acid is removed by rotary evaporator
  3. dissolutionthe residue dissolved in water (250 ml)
  4. additionThe solution is brought to approximate neutrality by addition of saturated aqueous sodium bicarbonate
  5. stirringstirred for 3 hours
  6. filtrationThe precipitate is filtered off
  7. washrinsed three times with water
  8. customdried
  9. customtriturated
  10. temperaturecooled
  11. filtrationfiltered off
  12. customdried

Sources & evidence

ORD record
ord-1e2a160a1f6b468f92308fdb38eea589
Source dataset
uspto-grants-1993_05
Patent number
US05208250

Reaction notes

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