Diethyl Ether → HCID 53754097, compound

HRID 1588476Notes

Reaction equation

HRID 1588476 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[Na].[N+](C1C=CC(S[C:17]2[C:22]([C:23]#[N:24])=[CH:21][C:20]([CH:25]=[CH:26][C:27]3[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:34])=[CH:19][N:18]=2)=CC=1)([O-])=O.C(OCC)C>C(O)(C)(C)C>[NH2:4][C:3]1[N:5]=[C:23]([NH2:24])[C:22]2[CH:21]=[C:20]([CH:25]=[CH:26][C:27]3[C:28]([Cl:34])=[CH:29][CH:30]=[CH:31][C:32]=3[Cl:33])[CH:19]=[N:18][C:17]=2[N:2]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 53756067HCID 53756067, compound

Product 1

HCID 53754097HCID 53754097, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
24 °C

Procedure

To a solution of 2.24 g (23.4 mM) of guanidine hydrochloride in 30 ml of tert.-butanol were added 0.538 g (23.4 mM) of sodium metal. The mixture was heated at 50° C. for 90 minutes, at which time 2.0 g (4.67 mM) of the 2-(4-nitrophenylthio)-3-cyano-5-(2,6-dichlorophenyl)ethenylpyridine from above were added in one portion. The mixture was heated at reflux for three hours, then cooled to 24° C., diluted by addition of 200 ml of diethyl ether, and filtered. The filter cake was washed with 30 ml of water and dried. The solid product was next washed with 20 ml of acetone and dried to afford 1.45 g (93.5% yield)

Workup

  1. additionfrom above were added in one portion
  2. temperatureThe mixture was heated
  3. temperatureat reflux for three hours
  4. filtrationfiltered
  5. washThe filter cake was washed with 30 ml of water
  6. customdried
  7. washThe solid product was next washed with 20 ml of acetone
  8. customdried
  9. customto afford 1.45 g (93.5% yield)

Sources & evidence

ORD record
ord-7e1501e6c11541cd920676540f307d41
Source dataset
uspto-grants-1993_06
Patent number
US05223503

Reaction notes

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