3,4-Dichlorophenyl isocyanate → HCID 23624263, compound

HRID 1919774Notes

Reaction equation

HRID 1919774 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([NH:24][CH2:25][CH:26]=[CH2:27])[C:20](OC)=[O:21])=[CH:15][CH:14]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:20](=[O:21])[CH:19]([C:16]3[CH:17]=[CH:18][C:13]([OH:12])=[CH:14][CH:15]=3)[N:24]([CH2:25][CH:26]=[CH2:27])[C:10]2=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 76073,4-Dichlorophenyl isocyanateHCID 62353665HCID 62353665, compound

Product 1

HCID 23624263HCID 23624263, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.1 equivalent of 3,4-dichlorophenyl isocyanate is added to a solution of 3.5 g of methyl 2-(4-hydroxyphenyl)-2-(2-propenyl)aminoacetate in 50 mL of anhydrous THF in a 50 mL flask equipped with a magnetic stirrer, under nitrogen. After heating under reflux for 4 hours, the product is concentrated then crystallised in isopropyl ether. The solid is filtered and washed with isopropyl ether to yield 3.2 g of white powder (Yd=54%).

Workup

  1. customequipped with a magnetic stirrer, under nitrogen
  2. temperatureAfter heating
  3. temperatureunder reflux for 4 hours
  4. concentrationthe product is concentrated
  5. customthen crystallised in isopropyl ether
  6. filtrationThe solid is filtered
  7. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-ff42e34aeba943299aef34b3bfbcf865
Source dataset
uspto-grants-2012_05
Patent number
US08168667B2

Reaction notes

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