Dimethyl Sulfoxide → HCID 70418021, compound

HRID 542943Notes

Reaction equation

HRID 542943 reaction equation
C[O-].[Na+].[NH:4]([CH2:11][CH2:12][C:13]#[N:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O[CH:16]([C:22]1[CH:32]=[C:31]([O:33][CH3:34])[C:25]([N:26]([CH3:30])[C:27](=[O:29])[CH3:28])=[C:24]([O:35][CH3:36])[CH:23]=1)CS(C)(=O)=O.CS(C)=O>O>[NH:4]([CH:11]=[C:12]([C:13]#[N:14])[CH2:16][C:22]1[CH:32]=[C:31]([O:33][CH3:34])[C:25]([N:26]([CH3:30])[C:27](=[O:29])[CH3:28])=[C:24]([O:35][CH3:36])[CH:23]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 21280987HCID 21280987, compound

Product 1

HCID 70418021HCID 70418021, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.24 g. of sodium methylate, 8.75 g. of β-anilino-propionitrile and 14.9 g. of 4'-[1-hydroxy-2-(methylsulfonyl)-ethyl]-2',6'-dimethoxy-N-methyl-acetanilide in 60 ml. of absolute dimethylsulfoxide was stirred at 50° C. for 4 hours with the exclusion of moisture. The solution was poured into 600 ml. of water. The resulting emulsion was extracted with two 400 ml. portions of ethyl acetate. Thereafter, the ethyl acetate extracts were washed with two 150 ml. portions of water, combined, dried over magnesium sulfate and evaporated under vacuum. Recrystallization of the residue from ethyl acetate gave 4'-(3-anilino-2-cyano-allyl)-2',6'-dimethoxy-N-methyl-acetanilide having a melting point of 202°-204° C.

Workup

  1. additionA mixture of 3.24 g
  2. additionThe solution was poured into 600 ml
  3. extractionThe resulting emulsion was extracted with two 400 ml
  4. washThereafter, the ethyl acetate extracts were washed with two 150 ml
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum
  7. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-f1c69459dc154a5d9383dd49fb159881
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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