Hydrochloric Acid → HCID 20273624, compound

HRID 371319Notes

Reaction equation

HRID 371319 reaction equation
C[O:2]C1C=C(C)C=CC=1C=S.[N+:12]([CH2:15][CH3:16])([O-])=O.C(N)CCC.Cl.[CH3:23][O:24][C:25]1[CH:30]=[C:29]([S:31][CH3:32])[CH:28]=[CH:27][C:26]=1[CH2:33][C:34](=O)[CH3:35].C[O:38][CH:39](OC)[N:40](C)C.CN(C)C=C(C1C=CC(SC)=CC=1OC)C(=O)C.C(CC(N)=O)#N>C1(C)C=CC=CC=1.C(O)(=O)C.[Fe]>[NH2:12][C:15]1[C:39](=[O:38])[NH:40][C:34]([CH3:35])=[C:33]([C:26]2[CH:27]=[CH:28][C:29]([S:31]([CH3:32])=[O:2])=[CH:30][C:25]=2[O:24][CH3:23])[CH:16]=1

Participants

12

Reactant 8

HCID 313Hydrochloric AcidHCID 6587NitroethaneHCID 7898CyanoacetamideHCID 8007ButylamineHCID 78373Dimethylformamide dimethyl acetalHCID 20273627HCID 20273627, compoundHCID 202736291-[2-Methoxy-4-(methylsulfanyl)phenyl]propan-2-oneHCID 537998114-(Dimethylamino)-3-[2-methoxy-4-(methylsulfanyl)phenyl]but-3-en-2-one

Product 1

HCID 20273624HCID 20273624, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

The starting material 1,2-dihydro-5-(2-methoxy-4-methylthiophenyl)-6-methyl-2-oxonicotinamide (m.p. 278°-281° [dec.]--from methylene chloride/methanol) is obtained by heating to ebullition 2-methoxy-4-methylthiobenzaldehyde with nitroethane in toluene in the presence of n-butylamine, converting the resultant nitrovinyl compound with iron powder and hydrochloric acid without further characterization to 1-(2-methoxy-4-methylthiophenyl)-2-propanone (b.p. 0.02 mm Hg=140°-150°), heating this compound with N,N-dimethylformamide dimethyl acetal for 3 hours to 80° and reacting the resultant 4-dimethylamino-3-(2-methoxy-4-methylthiophenyl)-3-buten-2-one (m.p. 111°-112°--from ether/petroleum ether) with cyanacetamide in glacial acetic acid at 100°.

Workup

  1. temperatureby heating
  2. customat 100°

Sources & evidence

ORD record
ord-99e14c46b8254096bc7694e865e172f9
Source dataset
uspto-grants-1985_07
Patent number
US04530842

Reaction notes

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