3,4-Dihydroxybenzaldehyde → 3-Amino-2-[(3-hydroxy-4-oxo-1-cyclohexa-2,5-dienylidene)methyl]-3-mercapto-2-propenenitrile

HRID 895952Notes

Reaction equation

HRID 895952 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]([NH2:16])=[S:15])#[N:12]>C(O)C.N1CCCCC1>[C:11]([C:13](=[CH:5][C:4]1[CH:7]=[CH:8][C:9]([OH:10])=[C:2]([OH:1])[CH:3]=1)[C:14](=[S:15])[NH2:16])#[N:12]

Participants

5

Reactant 2

HCID 87683,4-DihydroxybenzaldehydeHCID 14162772-Cyanoethanethioamide

Product 1

HCID 30347973-Amino-2-[(3-hydroxy-4-oxo-1-cyclohexa-2,5-dienylidene)methyl]-3-mercapto-2-propenenitrileYield 41%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To 0.83 g (6mmol) 3,4-dihydroxybenzaldehyde and 0.7 g (7 mmol) cyanothioacetamide in 30 ml ethanol was added 4 drops of piperidine. The mixture was refluxed for 1 hour, poured into ice water, filtered and dried, giving 0.54 g (41% yield) of an orange solid, m.p. 213° C. Calculated analysis for C10H8N2O2S: C=54.54, H=3.64, N=12.73; found: C=54.44, H=3.87, N=12.91.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-6be189d495e749f78f3a85872768450c
Source dataset
uspto-grants-2005_07
Patent number
USRE038761E1

Reaction notes

Loading…