Hydrogen Peroxide → HCID 54353810, compound

HRID 1439330Notes

Reaction equation

HRID 1439330 reaction equation
[NH2:1][C:2]([O:9][CH2:10][CH3:11])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(OCC)C.[O:17]([C:24]([N:26]=[C:27]=[S:28])=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.OO>C(O)C>[CH2:10]([O:9][C:2]1[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:27]([NH:26][C:24](=[O:25])[O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[S:28][N:1]=1)[CH3:11]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 3283Diethyl EtherHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 12212046Phenoxycarbonyl isothiocyanate

Product 1

HCID 54353810HCID 54353810, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 66.1 g of ethyl 3-amino-3-ethoxyacrylate and 300 ml of diethyl ether was stirred in a 500 ml flask during the addition of 60.5 g of phenoxycarbonylisothiocyanate. A solution of 38.3 ml of 33% hydrogen peroxide (11.5 g of active H2O2) in 300 ml of ethanol was added to the reaction mixture at a rate sufficient to maintain uniform reflux. The reaction mixture was allowed to stand at ambient temperature over a weekend. The precipitate was collected by filtration and dried. The filter cake was recrystallized from 1400 ml of 1:1 acetonitrile:water to yield 44.1 g of phenyl (3-ethoxy-4-ethoxycarbonyl-5-isothiazolyl)carbamate, mp 130° (decomposes). The ir spectrum was consistent with the assigned structure.

Workup

  1. temperatureto maintain uniform reflux
  2. waitto stand at ambient temperature over a weekend
  3. filtrationThe precipitate was collected by filtration
  4. customdried
  5. customThe filter cake was recrystallized from 1400 ml of 1:1 acetonitrile

Sources & evidence

ORD record
ord-85ed17e88c4a42209ac996f1d3b2a0a0
Source dataset
uspto-grants-1977_11
Patent number
US04059433

Reaction notes

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