Methyl Acrylate → HCID 14294150, compound

HRID 2073363Notes

Reaction equation

HRID 2073363 reaction equation
[CH3:1][C:2]([CH3:13])([CH3:12])[CH2:3][C:4]([NH:6][NH:7][C:8]([O:10][CH3:11])=[O:9])=[S:5].[C:14]([O:18][CH3:19])(=[O:17])[CH:15]=[CH2:16].C(N(CC)CC)C>C1C=CC=CC=1>[CH3:19][O:18][C:14](=[O:17])[CH2:15][CH2:16][S:5]/[C:4](=[N:6]\[NH:7][C:8]([O:10][CH3:11])=[O:9])/[CH2:3][C:2]([CH3:13])([CH3:12])[CH3:1]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 14294116HCID 14294116, compound

Product 1

HCID 14294150HCID 14294150, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 20.5 g of 2-(3,3-dimethyl-1-thioxobutyl)hydrazinecarboxylic acid, methyl ester, 12.92 g of methyl acrylate, 1 ml of triethylamine and 300 ml of dry benzene was heated at reflux for 8 hours, then cooled and concentrated in vacuo. The residual oil was chromatographed through a bed of hydrous magnesium silicate, eluting with dichloromethane and evaporated, giving 27 g of (Z)-[1-[(3-methoxy-3-oxopropyl)thio]-3,3-dimethylbutylidene]hydrazinecarboxylic acid, methyl ester.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe residual oil was chromatographed through a bed of hydrous magnesium silicate
  6. washeluting with dichloromethane
  7. customevaporated

Sources & evidence

ORD record
ord-d575da518d1c4f1b9f9a76a82d4adcb2
Source dataset
uspto-grants-1990_04
Patent number
US04916237

Reaction notes

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