Ethyl isocyanatoacetate → HCID 57070740, compound

HRID 1195963Notes

Reaction equation

HRID 1195963 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:2]=[O:3].[OH:10][C:11]1[CH:12]=[C:13]([CH:21]=[CH:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1[OH:17]>O1CCCC1>[CH2:8]([O:7][C:5]([CH2:4][NH:1][C:2]([O:10][C:11]1[CH:12]=[C:13]([CH:21]=[CH:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1[OH:17])=[O:3])=[O:6])[CH3:9]

Participants

4

Reactant 2

HCID 76283Ethyl isocyanatoacetateHCID 53849680HCID 53849680, compound

Product 1

HCID 57070740HCID 57070740, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

1.5 g of ethyl isocyanatoacetate was added to a solution containing 0.54 g of the product obtained in Example 8 in 10 ml of tetrahydrofuran and the solution was stirred for 3 days at 20° C. The solvent was evaporated in reduced pressure and the raw product was purified in a silica gel column using toluene-dioxane-acetic acid (8:1:1) as an eluent. Crystallization from acetone-petroleum ether yielded 0.13 g (17%) of the desired product desired, m.p 155°-158° C.

Workup

  1. customThe solvent was evaporated in reduced pressure
  2. customthe raw product was purified in a silica gel column
  3. customCrystallization from acetone-petroleum ether

Sources & evidence

ORD record
ord-9102c7127dee409ca78f6d85ff131cad
Source dataset
uspto-grants-1992_05
Patent number
US05112861

Reaction notes

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