Dimethyl Sulfoxide → 4-(3-Anilino-2-cyano-allyl)-2,6-dimethoxy carbanilic acid ethyl ester

HRID 462524Notes

Reaction equation

HRID 462524 reaction equation
CC[O-].[Na+].[NH:5]([CH2:12][CH2:13][C:14]#[N:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:16]([O:18][C:19](=[O:38])[NH:20][C:21]1[C:26]([O:27][CH3:28])=[CH:25][C:24]([CH:29](O)CS(C)(=O)=O)=[CH:23][C:22]=1[O:36][CH3:37])[CH3:17].CS(C)=O>O>[CH2:16]([O:18][C:19](=[O:38])[NH:20][C:21]1[C:26]([O:27][CH3:28])=[CH:25][C:24]([CH2:29][C:13]([C:14]#[N:15])=[CH:12][NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:23][C:22]=1[O:36][CH3:37])[CH3:17]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 141003-AnilinopropionitrileHCID 2723922Sodium ethoxideHCID 54348534HCID 54348534, compound

Product 1

HCID 704180124-(3-Anilino-2-cyano-allyl)-2,6-dimethoxy carbanilic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.42 g. of sodium ethylate, 5.1 g. of β-anilino-propionitrile and 10.0 g. of 4-[1-hydroxy-2-(methylsulfonyl)-ethyl]-2,6-dimethoxy-carbanilic acid ethyl ester in 150 ml. of dimethylsulfoxide was stirred at 50° C. for 2 hours with the exclusion of moisture. The solution was poured into 1.5 liters of water and the resulting emulsion extracted with two 1 liter portions of ethyl acetate. The ethyl acetate extracts were washed with two 500 ml. portions of water, combined, dried over magnesium sulfate and evaporated under vacuum. The residue was chromatographed on 800 g. of silica gel using methylene chloride/ethyl acetate (3:1) and there was obtained 4-(3-anilino-2-cyano-allyl)-2,6-dimethoxy-carbanilic acid ethyl ester having a melting point of 150°-151° C. (recrystallization from alcohol).

Workup

  1. additionA mixture of 4.42 g
  2. extractionthe resulting emulsion extracted with two 1 liter portions of ethyl acetate
  3. washThe ethyl acetate extracts were washed with two 500 ml
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under vacuum
  6. customThe residue was chromatographed on 800 g

Sources & evidence

ORD record
ord-1fda12dae8f44f5b845d9741eb7f45a2
Source dataset
uspto-grants-1985_05
Patent number
US04515948

Reaction notes

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