3,4-Dihydroxybenzaldehyde → HCID 136331475, compound

HRID 1587460Notes

Reaction equation

HRID 1587460 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.[C:11]([CH2:13][C:14]([NH:16][C:17]([NH2:19])=[O:18])=[O:15])#[N:12]>C(O)C.N1CCCCC1>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[N:19][C:17](=[O:18])[NH:16][C:14](=[O:15])[CH2:13][C:11]#[N:12]

Participants

5

Reactant 2

HCID 87683,4-DihydroxybenzaldehydeHCID 74055Acetamide, N-(aminocarbonyl)-2-cyano-

Product 1

HCID 136331475HCID 136331475, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To 0.69 g (5 mmol) 3,4-dihydroxybenzaldehyde and 0.6 g (5.3 mmol) cyanoacetylurea in 40 ml ethanol was added 2 drops piperidine. The reaction mixture was refluxed for 2 hours, cooled, filtered and washed with cold ethanol to yield 0.75 g (60% yield) of a yellow-orange solid, m.p. 235° C. (decomposition).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washwashed with cold ethanol

Sources & evidence

ORD record
ord-58f0a97e644f4b60af08e49eec08a88e
Source dataset
uspto-grants-1993_06
Patent number
US05217999

Reaction notes

Loading…