Toluene → HCID 18618207, compound

HRID 1264158Notes

Reaction equation

HRID 1264158 reaction equation
C[C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[C:4]([NH2:10])[C:3]=1[Br:11].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16].[C:20]1(C)C=CC=CC=1>>[Br:11][C:3]1[C:4]([N:10]=[CH:14][N:15]([CH3:17])[CH3:16])=[C:5]([C:7]([O:9][CH3:20])=[O:8])[S:6][CH:2]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 78373Dimethylformamide dimethyl acetalHCID 18618212HCID 18618212, compound

Product 1

HCID 18618207HCID 18618207, compound

Procedure

A solution of methyl 3-amino-4-bromo-2-thenoic acid (for preparator, see J. Gen. Chem. USSR, (1964), 34, 961) (5 g) and N,N-dimethylformamide dimethyl acetal (5 g) in toluene (30 ml) were heated under reflux for 8 hours. On cooling the solvent was removed and the residue purified by silica gel chromatography eluting with ethyl acetate: light petroleum (b.p. 60-80° C.) (1:3) to give the title compound.

Workup

  1. temperatureunder reflux for 8 hours
  2. temperatureOn cooling the solvent
  3. customwas removed
  4. customthe residue purified by silica gel chromatography
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-a4e43ceac95c431f860f8a247bc7ee69
Source dataset
uspto-grants-2003_04
Patent number
US06541630B1

Reaction notes

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