Sulfuric Acid → HCID 178496918, compound

HRID 1770082Notes

Reaction equation

HRID 1770082 reaction equation
C([C:3]([C:17]([O:19][CH3:20])=[O:18])=[C:4]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[CH:5]=[CH:6][N:7](C)[CH3:8])#N.S(=O)(=O)(O)[OH:22]>>[CH3:20][O:19][C:17](=[O:18])[C:3]1[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[CH:5][CH:6]=[N:7][C:8]=1[OH:22]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 54517867HCID 54517867, compound

Product 1

HCID 178496918HCID 178496918, compoundYield 60.9%

Procedure

117.0 g (0.54 mol) of 1-cyano-1-methoxycarbonyl-4-(N,N-dimethylamino)-2-(4-methylphenyl)-1,3-butadiene was added to 250 ml of concentrated sulfuric acid at a temperature below 20° C. under stirring, and the mixture was stirred at room temperature for 48 hours. The reaction mixture was poured into 1 l of ice water, and the precipitated material was filtrated out. The filtrate was adjusted to pH 6 with sodium hydroxide aqueous solution to precipitate the aimed product, which was then filtrated out. The material thus precipitated was washed with water and methanol, and was dried to obtain 74.9 g of a white crystal of the aimed product.

Workup

  1. stirringthe mixture was stirred at room temperature for 48 hours
  2. filtrationthe precipitated material was filtrated out
  3. customto precipitate the aimed product, which
  4. filtrationwas then filtrated out
  5. customThe material thus precipitated
  6. washwas washed with water and methanol
  7. customwas dried

Sources & evidence

ORD record
ord-403952ad6f5142cb8f8b80f0410ba93a
Source dataset
uspto-grants-1995_01
Patent number
US05385880

Reaction notes

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